2,3-二氢苯并呋喃-2-甲醇 | 66158-96-1

• 物质功能分类: 有机原料 - 杂环化合物
• 分子结构分类: 有机化合物 - 有机杂环化合物 - 香豆素
• 中文名称: 2,3-二氢苯并呋喃-2-甲醇
• 中文别名: 2,3-二氢-1-苯并呋喃-2-甲醇
• 英文名称: 2-hydroxymethyl-1H-2,3-dihydrobenzofuran
• 英文别名: 2-hydroxymethyl-2,3-dihydrobenzo(b)-furan；(+/-)-2-hydroxymethyl-2,3-dihydrobenzofuran；2,3-dihydro-2-(hydroxymethyl)benzofuran；(2,3-dihydro-benzofuran-2-yl)methanol；(2,3-dihydrobenzofuran-2-yl)methanol；2,3-dihydrobenzofuran-2-yl-methanol；2,3-dihydro-1-benzofuran-2-ylmethanol
• CAS: 66158-96-1
• 化学式: C₉H₁₀O₂
• mdl: MFCD03086171
• 分子量: 150.177
• InChiKey: ITMGMSZDAOAVNO-UHFFFAOYSA-N

物化性质

• 沸点：
  120-122
• 密度：
  1.181 g/cm3(Temp: 16 °C)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  2

安全信息

• 危险等级：
  IRRITANT
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• 海关编码：
  2932999099
• 安全说明：
  S24/25
• 储存条件：
  2-8°C

SDS

Name:	2 3-Dihydro-1-benzofuran-2-ylmethanol 90+% Material Safety Data Sheet
Synonym:
CAS:	66158-96-1

Section 1 - Chemical Product MSDS Name:2 3-Dihydro-1-benzofuran-2-ylmethanol 90+% Material Safety Data Sheet
Synonym:

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
66158-96-1	2,3-Dihydro-1-benzofuran-2-ylmethanol	90%+	unlisted

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

---

Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
Not available.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
Not available.

---

Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes.
Ingestion:
Get medical aid. Wash mouth out with water.
Inhalation:
Remove from exposure and move to fresh air immediately.
Notes to Physician:
Treat symptomatically and supportively.

---

Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

---

Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Absorb spill with inert material (e.g. vermiculite, sand or earth), then place in suitable container. Vacuum or sweep up material and place into a suitable disposal container.

---

Section 7 - HANDLING and STORAGE
Handling:
Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes.
Storage:
Store in a cool, dry place. Store in a tightly closed container.

---

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 66158-96-1: Personal Protective Equipment Eyes: Not available.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid or liquid
Color: Not available.
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: Not available.
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H10O2
Molecular Weight: 150.18

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Not available.
Conditions to Avoid:
Incompatible materials.
Incompatibilities with Other Materials:
Strong oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: Has not been reported

---

Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 66158-96-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
2,3-Dihydro-1-benzofuran-2-ylmethanol - Not listed by ACGIH, IARC, or NTP.

---

Section 12 - ECOLOGICAL INFORMATION

---

Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

---

Section 14 - TRANSPORT INFORMATION

IATA
No information available.
IMO
No information available.
RID/ADR
No information available.

---

Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 66158-96-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 66158-96-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 66158-96-1 is not listed on the TSCA inventory.
It is for research and development use only.

---

SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  2,3-二氢苯并呋喃-2-甲醇 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 碳酸氢钠 、 potassium bromide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 3.0h， 以77%的产率得到苯并二氢呋喃-2-羧酸
  参考文献：
  名称：

  苯并呋喃和2,3-二氢苯并呋喃-2-羧酸N-（取代）苯酰胺衍生物作为抗癌剂和NF-κB抑制剂的设计，合成和生物学评估

  摘要：

  为了开发新型支架作为抗癌剂和NF-κB活性抑制剂，开发了60种新颖的苯并呋喃和2,3-二氢苯并呋喃-2-羧酸N-（取代）苯酰胺衍生物（1a - s，2a - k，3a – s和4a – k）是由参考铅化合物KL-1156设计和合成的，它是LPS刺激的RAW 264.7巨噬细胞中NF-κB易位至细胞核的抑制剂。新型苯并呋喃-和2,3-二氢苯并呋喃-2-羧酰胺衍生物在低微摩尔浓度下对六种人类癌细胞系表现出强力的细胞毒性活性（通过磺基罗丹明B测定）：ACHN（肾），HCT15（结肠），MM231（乳腺），NUGC-3（胃），NCI-H23（肺）和PC-3（前列腺）。此外，这些化合物还抑制LPS诱导的NF-κB转录活性。N-苯环上的+ M效应和疏水基团分别增强了其抗癌活性和NF-κB抑制活性。然而，根据结构-活性关系研究的结果，只有苯并呋喃-2-羧酸N-（4'-羟基）苯酰胺（3m）是具有出色的抗癌

  DOI：

  10.1016/j.bmcl.2015.04.050
• 作为产物：
  描述：

  2-烯丙基酚 在 poly(N-isopropylacrylamide)-based phosphotungstate complex 双氧水 作用下， 以 水 为溶剂， 反应 12.0h， 以71%的产率得到2,3-二氢苯并呋喃-2-甲醇
  参考文献：
  名称：

  利用温度响应催化剂的新型固相反应系统：过氧化氢的氧化环化

  摘要：

  基于温度变化的可转换催化剂在水中提供了一种新颖的固相反应系统。在较高温度下，对有机底物的催化剂亲和力的增加导致有效的活性驱动了固态内相反应，而在较低温度下亲和力的丧失使反应完成时有机产物易于分离。利用该催化剂智能设计新颖的催化系统，可利用过氧化氢进行有效的氧化环化反应，这是一种利用氧杂环的有效方法。

  DOI：

  10.1002/adsc.200700114

文献信息

• Gold-Catalysed Activation of Epoxides: Application in the Synthesis of Bicyclic Ketals
  作者：Rengarajan Balamurugan、Raveendra Babu Kothapalli、Ganesh Kumar Thota

  DOI：10.1002/ejoc.201001214

  日期：2011.3

  Gold-catalysed generation of diol equivalents from epoxides and their intramolecular reaction with C≡C bonds to generate bicyclic ketals is presented. This reaction essentially involves the formation of an acetonide, which subsequently cyclises on the alkyne intramolecularly under gold catalysis conditions. This method could be extended to make optically pure bicyclic ketals. Deuterium incorporation

  介绍了金催化从环氧化物生成二醇等价物及其与 C≡C 键的分子内反应生成双环缩酮。该反应主要涉及丙酮化物的形成，其随后在金催化条件下分子内在炔烃上环化。这种方法可以扩展到制造光学纯的双环缩酮。进行氘掺入实验以确定反应机理。
• [EN] (THIO)MORPHOLINE DERIVATIVES AS S1P MODULATORS<br/>[FR] DÉRIVÉS DE (THIO)MORPHOLINE MODULATEURS DE S1P
  申请人：ABBOTT HEALTHCARE PRODUCTS BV

  公开号：WO2011023795A1

  公开（公告）日：2011-03-03

  The present invention relates to (thio)morpholine derivatives of the formula (I), wherein R1 is selected from cyano, (2-4C)alkynyl, (1-4C)alkyl, (3-6C)cycloalkyl, (4-6C)cycloalkenyl, (6-8C)bicycloalkyl, (8-10C)bicyclic group, each optionally substituted with (1-4C)alkyl, phenyl, biphenyl, naphthyl, each optionally substituted with one or more substituents independently selected from halogen, (1-4C)alkyloptionally substituted with one or more fluoro atoms, (2-4C)alkynyl, (1-4C)alkoxy optionally substituted with one or more fluoro atoms,amino, di(1-4C)alkylamino, -SO2-(1-4C)alkyl, -CO-(1-4C)alkyl, -CO-O-(1-4C)alkyl, -NH-CO-(1-4C)alkyl and (3-6C)cycloalkyl, phenyl substituted with phenoxy, benzyl, benzyloxy, phenylethyl or monocyclic heterocycle, each optionally substituted with (1-4C)alkyl, monocyclic heterocycle optionally substituted with halogen, (1-4C)alkyl or with phenyl optionally substituted with (1-4C)alkyl, and bicyclic heterocycle optionally substituted with (1-4C)alkyl; A is selected from -CO-O-, -O-CO-, -NH-CO-, -CO-NH, -C=C-, -CCH3-O- and the linking group –Y-(CH2)n-X- wherein Y is attached to R1 and selected from a bond, -O-, -S-, -SO-, -SO2-, -CH2-O-, -CO-, -O-CO-, -CO-O-, -CO-NH-, -NH-CO-, -C=C-and -C≡C-; n is an integer from 1 to 10; and X is attached to the phenylene / pyridyl group and selected from a bond, -O-, -S-, -SO-, -SO2 -, -NH, -CO-, -C=C-and -C≡C-; ring structure B optionally contains one nitrogen atom; R2 is H, (1-4C)alkyl optionally substituted with one or more fluoro atoms, (1-4C)alkoxy optionally substituted with one or more fluoro atoms, or halogen; and R3 is (1-4C)alkylene-R5 wherein the alkylene group may be substituted with (CH2)2 to form a cyclopropyl moiety or one or two halogen atoms, or R3 is is (3-6C)cycloalkylene-R5 or -CO-CH2-R5, wherein R5 is -OH, -PO3H2, -OPO3H2, -COOH, -COO(1-4C)alkyl or tetrazol-5-yl; R4 is H or (1-4C)alkyl; R6 is one or more substituents independently selected from H, (1-4C)alkyl or oxo; W is -O-, -S-, -SO- or -SO2-; or a pharmaceutically acceptable salt, a solvate or hydrate thereof; with the proviso that the derivative of formula (I) is not 2-(4-ethylphenyl)-4-morpholinoethanol or 4-[4-(2-hydroxyethyl)-2-morpholinyl]benzeneacetonitrile or a pharmaceutically acceptable salt, a solvate or hydrate thereof. The compounds of the invention have affinity to S1P receptors and may be used in the treatment, alleviation or prevention of S1P receptor mediated diseases and conditions.

  本发明涉及公式（I）的（硫）吗啉衍生物，其中R1从氰基，（2-4C）炔基，（1-4C）烷基，（3-6C）环烷基，（4-6C）环烯基，（6-8C）双环烷基，（8-10C）双环基团中选择，每个基团可选择地取代为（1-4C）烷基，苯基，联苯基，萘基，每个基团可选择地取代为一个或多个取代基，独立选择自卤素，（1-4C）烷基可选择地取代为一个或多个氟原子，（2-4C）炔基，（1-4C）氧烷基可选择地取代为一个或多个氟原子，氨基，二（1-4C）烷基氨基，-SO2-（1-4C）烷基，-CO-（1-4C）烷基，-CO-O-（1-4C）烷基，-NH-CO-（1-4C）烷基和（3-6C）环烷基，苯基取代为苯氧基，苄基，苄氧基，苯乙基或单环杂环烃，每个基团可选择地取代为（1-4C）烷基，单环杂环烃可选择地取代为卤素，（1-4C）烷基或取代为苯基的苯基，可选择地取代为（1-4C）烷基，和双环杂环烃可选择地取代为（1-4C）烷基；A从-CO-O-，-O-CO-，-NH-CO-，-CO-NH，-C=C-，-CCH3-O-和连接基-Y-（CH2）n-X-中选择，其中Y连接到R1并从键，-O-，-S-，-SO-，-SO2-，-CH2-O-，-CO-，-O-CO-，-CO-O-，-CO-NH-，-NH-CO-，-C=C-和-C≡C-中选择；n是1到10的整数；X连接到苯基/吡啶基团并从键，-O-，-S-，-SO-，-SO2-，-NH，-CO-，-C=C-和-C≡C-中选择；环结构B可选择地含有一个氮原子；R2是H，（1-4C）烷基可选择地取代为一个或多个氟原子，（1-4C）氧烷基可选择地取代为一个或多个氟原子，或卤素；R3是（1-4C）烷基-R5，其中烷基基团可取代为（CH2）2形成环丙基基团或一个或两个卤素原子，或R3是（3-6C）环烷基-R5或-CO-CH2-R5，其中R5是-OH，-PO3H2，-OPO3H2，-COOH，-COO（1-4C）烷基或四唑-5-基；R4是H或（1-4C）烷基；R6是一个或多个取代基，独立选择自H，（1-4C）烷基或氧代基；W是-O-，-S-，-SO-或-SO2-；或其药学上可接受的盐，溶剂或水合物；但是，公式（I）的衍生物不是2-（4-乙基苯基）-4-吗啉乙醇或4-[4-（2-羟乙基）-2-吗啉基]苯乙腈或其药学上可接受的盐，溶剂或水合物。本发明的化合物具有对S1P受体的亲和力，可用于治疗、缓解或预防S1P受体介导的疾病和症状。
• Green Organocatalytic Synthesis of Dihydrobenzofurans by Oxidation–Cyclization of Allylphenols
  作者：Christoforos Kokotos、Ierasia Triandafillidi、Ioanna Sideri、Dimitrios Tzaras、Nikoleta Spiliopoulou

  DOI：10.1055/s-0036-1588998

  日期：2017.9

  dihydrobenzofurans via an organocatalytic oxidation of o-allylphenols is presented. The use of 2,2,2-trifluoroacetophenone and H2O2 as the oxidation system, leads to a highly useful synthetic method, where a variety of substituted o-allylphenols were cyclized in high yields. A green and cheap protocol for the synthesis of dihydrobenzofurans via an organocatalytic oxidation of o-allylphenols is presented. The use of

  作为专题“现代合成中的环化策略”的一部分发布 抽象的 提出了一种绿色廉价的方案，用于通过邻烯丙基苯酚的有机催化氧化合成二氢苯并呋喃。使用2,2,2-三氟苯乙酮和H 2 O 2作为氧化系统，导致了一种非常有用的合成方法，其中各种取代的邻烯丙基苯酚均以高收率环化。 提出了一种绿色廉价的方案，用于通过邻烯丙基苯酚的有机催化氧化合成二氢苯并呋喃。使用2,2,2-三氟苯乙酮和H 2 O 2作为氧化系统，导致了一种非常有用的合成方法，其中各种取代的邻烯丙基苯酚均以高收率环化。
• [EN] G PROTEIN-COUPLED RECEPTOR MODULATORS AND A PHARMACEUTICAL COMPOSITION<br/>[FR] MODULATEURS DU RÉCEPTEUR COUPLÉ À LA PROTÉINE G ET COMPOSITION PHARMACEUTIQUE
  申请人：UNIV COPENHAGEN

  公开号：WO2021123394A1

  公开（公告）日：2021-06-24

  The invention concerns a compound of formula I, a pharmaceutical formulation comprising the compound of formula I and use of the pharmaceutical composition for treating inflammatory or diabetic disease.

  这项发明涉及一种I式化合物，包括该I式化合物的药物配方以及将该药物组合物用于治疗炎症性或糖尿病疾病的用途。
• A Reversible and Selective Inhibitor of Monoacylglycerol Lipase Ameliorates Multiple Sclerosis
  作者：Gloria Hernández-Torres、Mariateresa Cipriano、Erika Hedén、Emmelie Björklund、Ángeles Canales、Debora Zian、Ana Feliú、Miriam Mecha、Carmen Guaza、Christopher J. Fowler、Silvia Ortega-Gutiérrez、María L. López-Rodríguez

  DOI：10.1002/anie.201407807

  日期：2014.12.8

  of MAGL inhibitors are needed to validate this enzyme as a therapeutic target. Here we report a potent, selective, and reversible MAGL inhibitor (IC50=0.18 μM) which is active in vivo and ameliorates the clinical progression of a multiple sclerosis (MS) mouse model without inducing undesirable CB1‐mediated side effects. These results support the interest in MAGL as a target for the treatment of MS

  单酰基甘油脂酶（MAGL）是负责内源性大麻素2-花生四烯酸甘油酯（2-AG）失活的酶。MAGL抑制剂在几种疾病模型中均具有镇痛和组织保护作用。然而，迄今为止描述的几种有效且选择性的MAGL抑制剂不可逆地阻断了该酶，并且这可能导致药理学耐受性。因此，还需要其他类别的MAGL抑制剂来验证该酶是否可作为治疗靶标。此处我们报告一个有效的，选择性，和可逆的抑制剂MAGL（IC 50 = 0.18μ中号），它是体内活性和改善多发性硬化（MS）的小鼠模型的临床进展，而不引起不希望的CB 1介导的副作用。这些结果支持了对MAGL作为MS治疗靶标的兴趣。

表征谱图