(1R,2R,3S,5R)-(-)-2,3-蒎烷二醇 | 22422-34-0

• 物质功能分类: 医药中间体 - 原料药中间体
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 中文名称: (1R,2R,3S,5R)-(-)-2,3-蒎烷二醇
• 中文别名: (1R-(1alpha,2beta,3beta,5alpha))-2,6,6-三甲基双环[3.3.1]庚烷-2,3-二醇；(1R,2R,3S,5R)-2,6,6-三甲基二环[3.1.1]庚-2,3-二醇；(1R,2R,3S,5R)-(-)-蒎二醇；(1R,2R,3S,5R)-(-)-蒎烷二醇；三甲基庚烷二醇
• 英文名称: (1R,2R,3S,5R)-2,3-pinane diol
• 英文别名: (1R,2R,3S,5R)-(-)-pinanediol；(-)-pinanediol；(1R,2R,3S,5R)-2,6,6-trimethylbicyclo[3.1.1]heptane-2,3-diol；(1R,2R,3S,5R)-(-)-pinane-2,3-diol；(-)-pinandiol；(1R,2R,3S,5R)-(-)-2,3-Pinanediol
• CAS: 22422-34-0
• 化学式: C₁₀H₁₈O₂
• mdl: MFCD09955216
• 分子量: 170.252
• InChiKey: MOILFCKRQFQVFS-BDNRQGISSA-N

物化性质

• 熔点：
  57-59 °C(lit.)
• 比旋光度：
  -8.5 º (c=6.5, toluene)
• 沸点：
  101-102 °C1 mm Hg(lit.)
• 密度：
  0.9409 (rough estimate)
• 闪点：
  >230 °F
• 溶解度：
  可溶于氯仿、甲醇、甲苯
• LogP：
  1.582 (est)
• 稳定性/保质期：
  遵照规定使用和储存，则不会分解。

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 安全说明：
  S24/25
• 危险品运输编号：
  NONH for all modes of transport
• 海关编码：
  2942000000
• 危险品标志：
  Xi
• 危险类别码：
  R36/37/38
• WGK Germany：
  3
• 危险性防范说明：
  P261,P264,P271,P280,P302+P352,P304+P340,P305+P351+P338,P312,P362,P403+P233,P501
• 危险性描述：
  H315,H319,H335
• 储存条件：
  存放于阴凉干燥处。

SDS

Name:	(1R 2R 3S 5R)-(-)-2 3-Pinanediol 98% Material Safety Data Sheet
Synonym:
CAS:	22422-34-0

Section 1 - Chemical Product MSDS Name:(1R 2R 3S 5R)-(-)-2 3-Pinanediol 98% Material Safety Data Sheet
Synonym:

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
22422-34-0	(1R,2R,3S,5R)-(-)-2,3-Pinanediol	98%	unlisted

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

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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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. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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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. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion. Runoff from fire control or dilution water may cause pollution.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam. Use agent most appropriate to extinguish fire.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Clean up spills immediately, observing precautions in the Protective Equipment section. Avoid generating dusty conditions.
Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Use with adequate ventilation.
Minimize dust generation and accumulation. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing.
Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Store in a cool, dry, well-ventilated area away from incompatible substances. Keep refrigerated. (Store below 4C/39F.)

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 22422-34-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
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.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: 101 - 102 deg C @ 1mmHg
Freezing/Melting Point: 57 - 59 deg C
Autoignition Temperature: Not applicable.
Flash Point: > 110 deg C (> 230.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C10H18O2
Molecular Weight: 170.25

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable at room temperature in closed containers under normal storage and handling conditions.
Conditions to Avoid:
Incompatible materials, dust generation, excess heat, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Carbon monoxide, irritating and toxic fumes and gases, carbon dioxide.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 22422-34-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(1R,2R,3S,5R)-(-)-2,3-Pinanediol - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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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.
S 28A After contact with skin, wash immediately with
plenty of water.
S 37 Wear suitable gloves.
S 45 In case of accident or if you feel unwell, seek
medical advice immediately (show the label where
possible).
WGK (Water Danger/Protection)
CAS# 22422-34-0: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 22422-34-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 22422-34-0 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,5R)-(-)-2,3-蒎烷二醇 在 4-二甲氨基吡啶 、 4-甲基苯磺酸吡啶 、 二异丁基氢化铝 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 36.0h， 生成 (1R,2R,3S,5R)-2,6,6-trimethyl-2-(naphthalen-1-ylmethoxy)bicyclo[3.1.1]heptan-3-yl 3,3,3-trifluoropropanoate
  参考文献：
  名称：

  3-（3,3-，3-三氟丙酸酯）不对称醛醇缩合反应中2-（芳基甲氧基）异opinocampheols的制备及应用

  摘要：

  已经描述了通过DIABL-H还原相应的芳基醛缩醛由pin烷二醇制备2-（芳基甲氧基）异opinocampheols。导致的2-双非对映选择性醛醇缩合反应的3,3,3- trifluoropropionates不对称醛醇缩合反应的系统的检查（芳基甲氧）isopinocampheyl 3,3,3- trifluoropropionates提供抗在63-α三氟甲基β羟基酯–85％的产率、, 99％的抗选择性和80–96％的抗异构体de 。

  DOI：

  10.1016/j.tetlet.2011.08.034
• 作为产物：
  描述：

  (+)-α-蒎烯 在 potassium permanganate 、 十二烷基三甲基氯化铵 、 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 生成 (1R,2R,3S,5R)-(-)-2,3-蒎烷二醇
  参考文献：
  名称：

  一种手性邻二醇的合成方法及其产品

  摘要：

  本发明提供了一种手性邻二醇的合成方法，包括以下步骤：(1)将作为该手性邻二醇的前体的烯烃与二氯甲烷加入到反应装置中，并加入碱；然后在‑50℃至‑15℃的温度下，加入相转移催化剂，再分批加入高锰酸钾或高锰酸钠进行反应，得中间体a；(2)将中间体a加入到反应装置中，搅拌下加入乙醚和石油醚，然后分批加入硼酸；滴加氢氧化钾的水溶液进行反应，得中间体b；(3)将所述中间体b加入到反应装置中，再加入乙醚和水，然后在冰浴冷却条件下，滴加氢氟酸，低温搅拌过夜，制得所述手性邻二醇。本发明使用了廉价的、毒性低的、且环境污染小的高锰酸钾或高锰酸钠作为反应试剂，实现了手性邻二醇类化合物的工业化合成生产。

  公开号：

  CN105859519B
• 作为试剂：
  描述：

  (1R,2R,3S,5R)-(-)-2,3-蒎烷二醇 、 硼酸,(4-溴丁基)-,二甲基酯 在 (1R,2R,3S,5R)-(-)-2,3-蒎烷二醇 作用下， 以98的产率得到(1R,2R,6S,8R)-4-(4-bromobutyl)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decane
  参考文献：
  名称：

  对映体羟基化黄嘌呤化合物

  摘要：

  本发明公开了在3，7-二取代黄嘌呤的1位上具有被直链烷基(C 5-8 )取代的W-1醇的拆分R或S(优选R)对映体的化合物和药组合物。本发明化合物能有效调节细胞对外部或原位刺激的应答，以及对给这种化合物的特定方式应答。

  公开号：

  CN1085557A

文献信息

• Enantiospecific Suzuki-Miyaura Coupling of Nonbenzylic α-(Acylamino)alkylboronic Acid Derivatives
  作者：Toshimichi Ohmura、Kyoko Miwa、Tomotsugu Awano、Michinori Suginome

  DOI：10.1002/asia.201800536

  日期：2018.9.4

  Suzuki–Miyaura coupling of nonbenzylic α‐(acylamino)alkylboron compounds with aryl halides is established. A Pd/PCy2Ph catalyst promotes the reaction efficiently at 145 °C. The reaction of enantioenriched α‐(acylamino)alkylboron compounds affords chiral 1‐arylalkylamides in high enantiospecificity and inversion of configuration.

  建立了非苄基α-（酰基氨基）烷基硼化合物与芳基卤化物的Suzuki-Miyaura偶联。Pd / PCy 2 Ph催化剂可在145°C的条件下有效地促进反应。富含对映体的α-（酰基氨基）烷基硼化合物的反应可提供高对映体特异性和构型反转的手性1-芳基烷基酰胺。
• [EN] ARGINASE INHIBITORS AND METHODS OF USE<br/>[FR] INHIBITEURS D'ARGINASE ET PROCÉDÉS D'UTILISATION
  申请人：MERCK SHARP & DOHME

  公开号：WO2019177873A1

  公开（公告）日：2019-09-19

  Described herein are compounds of Formula I or a pharmaceutically acceptable salt thereof. The compounds of Formula I act as arginase inhibitors and can be useful in preventing, treating or acting as a remedial agent for arginase-related diseases.

  本文描述了化合物I的结构或其药用盐。化合物I作为精氨酸酶抑制剂，可用于预防、治疗或作为精氨酸酶相关疾病的治疗剂。
• [EN] ALKYLBORONIC ACIDS AS ARGINASE INHIBITORS<br/>[FR] ACIDES ALKYLBORONIQUES EN TANT QU'INHIBITEURS D'ARGINASE
  申请人：GUANGDONG NEWOPP BIOPHARMACEUTICALS CO LTD

  公开号：WO2020160707A1

  公开（公告）日：2020-08-13

  Provided are alkylboronic acids as arginase inhibitors represented by formula (I), or a pharmaceutically acceptable salt, stereoisomer, tautomer, or prodrug thereof and a pharmaceutical composition comprising said compounds.

  提供的是以化学式(I)表示的烷基硼酸作为精氨酸酶抑制剂，或其药用可接受的盐、立体异构体、互变异构体或前药，以及包含该化合物的药物组合物。
• Cyclopropanation of Terminal Alkenes through Sequential Atom‐Transfer Radical Addition/1,3‐Elimination
  作者：Nicholas D. C. Tappin、Weronika Michalska、Simon Rohrbach、Philippe Renaud

  DOI：10.1002/anie.201907962

  日期：2019.10

  An operationally simple method to affect an atom-transfer radical addition of commercially available ICH2 Bpin to terminal alkenes has been developed. The intermediate iodide can be transformed in a one-pot process into the corresponding cyclopropane upon treatment with a fluoride source. This method is highly selective for the cyclopropanation of unactivated terminal alkenes over non-terminal alkenes

  已经开发出一种可操作的简单方法来影响将可商购的ICH2 Bpin原子转移自由基加成到末端烯烃上。在用氟化物源处理后，中间体碘化物可以一锅法转化为相应的环丙烷。该方法对于未活化的末端烯烃在非末端烯烃和缺电子的烯烃上的环丙烷化是高度选择性的。由于该过程温和，因此可以很好地耐受各种官能团，例如酯，酰胺，醇，酮和乙烯基环丙烷。
• A new chiral catalytic source with an N–PO structural framework containing a proximal hydroxyl group for the borane-mediated asymmetric reduction of prochiral ketones
  作者：Deevi Basavaiah、Gone Jayapal Reddy、Vanampally Chandrashekar

  DOI：10.1016/j.tetasy.2003.11.002

  日期：2004.1

  3S,5R)-2-Hydroxy-2,6,6-trimethylbicyclo[3.1.1]heptan-3-yloxy]-1,3-diaza-2-phospha-2-oxo-3-phenylbicyclo[3.3.0]octane has been successfully employed as a novel chiral catalytic source (4 mol %) for borane-mediated asymmetric reduction of prochiral ketones thus providing the resulting secondary alcohols with up to 96% enantiomeric excess.

  （5 S）-2-[（1 R，2 R，3 S，5 R）-2-羟基-2,6,6-三甲基双环[3.1.1]庚基-3-基氧基] -1,3-二氮杂-2-磷-2-氧代-3-苯基二环[3.3.0]辛烷已成功地用作新型手性催化源（4摩尔％），用于硼烷介导的前手性酮的不对称还原，从而使生成的仲醇具有较高的收率。对映体过量为96％。

表征谱图