(S)-1-苯基-1,3-丙二醇 | 96854-34-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (S)-1-苯基-1,3-丙二醇
• 中文别名: (1S,5R)-1-苯基-3-氧杂双环[3.1.0]己烷-2-酮
• 英文名称: (S)-3-phenyl-1,3-propanediol
• 英文别名: (S)-1-phenyl-1,3-propanediol；(1S)-1-phenylpropane-1,3-diol
• CAS: 96854-34-1
• 化学式: C₉H₁₂O₂
• 分子量: 152.193
• InChiKey: RRVFYOSEKOTFOG-VIFPVBQESA-N

物化性质

• 熔点：
  61-64 °C
• 沸点：
  234.66°C (rough estimate)
• 密度：
  1.0505 (rough estimate)
• 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)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  40.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2906299090
• 安全说明：
  S24/25
• 储存条件：
  存放于阴凉干燥处

SDS

Name:	(S)-1-Phenyl-1 3-propanediol Material Safety Data Sheet
Synonym:	alpha-Bromotoluene
CAS:	96854-34-1

Section 1 - Chemical Product MSDS Name:(S)-1-Phenyl-1 3-propanediol Material Safety Data Sheet
Synonym:alpha-Bromotoluene

---

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
96854-34-1	(S)-1-Phenyl-1,3-propanediol	ca.100	unlisted

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

---

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. May be harmful if absorbed through the skin.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated. May be harmful if swallowed.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated. May be harmful if inhaled.
Chronic:
No information found.

---

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 immediately.
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:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
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:
Treat symptomatically and supportively.
Antidote: None reported.

---

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.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

---

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

---

Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Minimize dust generation and accumulation. Avoid contact with eyes, skin, and clothing. Keep container tightly closed. Avoid ingestion and inhalation.
Storage:
Keep container closed when not in use. Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

---

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# 96854-34-1: 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.

---

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Powder and chunks
Color: white
Odor: Not available.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 62-66 deg C
Autoignition Temperature: Not available.
Flash Point: Not available.
Explosion Limits, lower: N/A
Explosion Limits, upper: N/A
Decomposition Temperature:
Solubility in water:
Specific Gravity/Density:
Molecular Formula: C9H12O2
Molecular Weight: 152.19

---

Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Dust generation.
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# 96854-34-1 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(S)-1-Phenyl-1,3-propanediol - 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
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
IMO
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing Group:
RID/ADR
Shipping Name: Not regulated.
Hazard Class:
UN Number:
Packing group:

---

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# 96854-34-1: No information available.
Canada
None of the chemicals in this product are listed on the DSL/NDSL list.
CAS# 96854-34-1 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 96854-34-1 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：

  (S)-1-苯基-1,3-丙二醇 在 盐酸 、 sodium hydride 、 三乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 水 、 丙酮 为溶剂， 生成 (3S)-N-甲基-3-苯基-3-[4-(三氟甲基)苯氧基]-1-丙胺盐酸盐(1:1)
  参考文献：
  名称：

  Chemoenzymatic Synthesis of Both Enantiomers of Fluoxetine

  摘要：

  氟西汀的两种对映体都是由苯甲酰乙酸乙酯合成的。关键步骤是用面包酵母对起始原料进行对映体选择性还原。

  DOI：

  10.1246/cl.1991.1603
• 作为产物：
  描述：

  (S)-1-苯基-3-丁烯-1-醇 在 sodium tetrahydroborate 、 臭氧 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 (S)-1-苯基-1,3-丙二醇
  参考文献：
  名称：

  高效烯丙基醇的酶促拆分，可轻松合成光学纯的氟西汀及其相关化合物

  摘要：

  报道了一种酶促拆分烯丙基醇的实用方法及其在合成光学纯氟西汀及其相关化合物中的实用性

  DOI：

  10.1016/s0040-4039(96)02136-3

文献信息

• Chiral Ion-Pair Organocatalyst-Promoted Efficient Enantio-selective Reduction of α-Hydroxy Ketones
  作者：Yiliang Zhang、Li He、Lei Shi

  DOI：10.1002/adsc.201800053

  日期：2018.5.16

  The enantioselective reduction of α‐hydroxy ketones with catecholborane has been developed employing 5 mol% of an 1,1′‐bi‐2‐naphthol (BINOL)‐derived ion‐pair organocatalyst. This methodology provides a straightforward access to the corresponding aromatic 1,2‐diols in high yields (up to 90%) with excellent enantioselectivities (up to 97%). Furthermore, the α‐amino ketones also could be reduced with

  已经开发了使用5摩尔％的1,1'-联-2-萘酚（BINOL）衍生的离子对有机催化剂对儿茶酚硼烷对α-羟基酮的对映选择性还原。该方法可直接获得相应的芳族1,2-二醇，且收率很高（高达90％），对映选择性极好（高达97％）。此外，在温和的反应条件下，中等ee值也可以还原α-氨基酮。
• Organic metal compound and process for preparing optically-active alcohols using the same
  申请人：Miki Takashi

  公开号：US20090062573A1

  公开（公告）日：2009-03-05

  The present invention provides an asymmetric reduction catalyst effective in preparing optically-active alcohol compounds having various functional groups, and a process for preparing optically-active alcohol compounds using said asymmetric reduction catalyst. The organic metal compound of the present invention is represented by the following general formula (1): wherein R 1 and R 2 may be mutually identical or different, and are an alkyl group, a phenyl group, a naphthyl group, a cycloalkyl group, or an alicyclic ring formed by binding R 1 and R 2 , which may have a substituent; R 3 is a hydrogen atom or an alkyl group; Cp is a cyclopentadienyl group, which may have a substituent, bound to M 1 via a π bond; X 1 is a halogen atom or a hydrido group; M 1 is rhodium or iridium; and * denotes asymmetric carbon.

  本发明提供了一种在制备具有各种官能团的光学活性醇化合物中有效的非对称还原催化剂，以及使用所述非对称还原催化剂制备光学活性醇化合物的方法。 本发明的有机金属化合物由以下通式(1)表示： 其中R1和R2可以相互相同或不同，并且是烷基、苯基、萘基、环烷基或由R1和R2结合形成的脂肪环环，其中可能含有取代基；R3是氢原子或烷基；Cp是环戊二烯基，可能含有取代基，通过π键与M1结合；X1是卤素原子或氢化物基团；M1是铑或铱；*表示不对称碳。
• Identification of potent type I MetAPs inhibitors by simple bioisosteric replacement. Part 2: SAR studies of 5-heteroalkyl substituted TCAT derivatives
  作者：Yong-Mei Cui、Qing-Qing Huang、Jie Xu、Ling-Ling Chen、Jing-Ya Li、Qi-Zhuang Ye、Jia Li、Fa-Jun Nan

  DOI：10.1016/j.bmcl.2005.06.005

  日期：2005.9

  Systematic SAR studies on the thiazole ring 5-substituent of TCAT derivatives revealed that the introduction of a beta-alkoxy or an amino group enhanced the inhibitory activity significantly. The present compounds are representative of specific Co(II)-MetAP1 inhibitors. Before the physiologically relevant metal ions for MetAPs are established, these small molecular compounds could be used as tools

  对TCAT衍生物的噻唑环5取代基进行的系统SAR研究表明，引入β-烷氧基或氨基可显着提高其抑制活性。本发明化合物代表特定的Co（II）-MetAP1抑制剂。在建立MetAP的生理相关金属离子之前，这些小分子化合物可以用作进行详细生物学研究的工具。
• Organocatalytic Direct Asymmetric Crossed-Aldol Reactions of Acetaldehyde in Aqueous Media
  作者：Yupu Qiao、Qiankun Chen、Sirong Lin、Bukuo Ni、Allan D. Headley

  DOI：10.1021/jo302442g

  日期：2013.3.15

  dioctylamino group in the presence of a newly developed ionic liquid supported (ILS) benzoic acid as cocatalyst, is shown to be an effective catalytic system for the asymmetric direct crossed-aldol reaction of acetaldehyde in aqueous media using brine. For the reactions studied, the catalyst loading could be reduced to 5 mol %; high yields (up to 97%) and high enantioselectivities (up to 92% ee) were also

  一种新型的基于二芳基脯氨醇的新型催化剂，在新开发的离子液体负载的（ILS）苯甲酸作为助催化剂的存在下，含有二辛基氨基，是一种有效的催化体系，用于乙醛的不对称直接交叉-羟醛反应在盐水中的水性介质中。对于所研究的反应，催化剂的载量可以降低至5mol％；优选地，催化剂的载量可以降低至5mol％。对于多种芳族醛，还实现了高收率（高达97％）和高对映选择性（高达92％ee）。
• Structure-Based Design and Synthesis of 1,3-Oxazinan-2-one Inhibitors of 11β-Hydroxysteroid Dehydrogenase Type 1
  作者：Zhenrong Xu、Colin M. Tice、Wei Zhao、Salvacion Cacatian、Yuan-Jie Ye、Suresh B. Singh、Peter Lindblom、Brian M. McKeever、Paula M. Krosky、Barbara A. Kruk、Jennifer Berbaum、Richard K. Harrison、Judith A. Johnson、Yuri Bukhtiyarov、Reshma Panemangalore、Boyd B. Scott、Yi Zhao、Joseph G. Bruno、Jennifer Togias、Joan Guo、Rong Guo、Patrick J. Carroll、Gerard M. McGeehan、Linghang Zhuang、Wei He、David A. Claremon

  DOI：10.1021/jm2005354

  日期：2011.9.8

  Structure based design led directly to 1,3-oxazinan-2-one 9a with an IC50 of 42 nM against 11β-HSD1 in vitro. Optimization of 9a for improved in vitro enzymatic and cellular potency afforded 25f with IC50 values of 0.8 nM for the enzyme and 2.5 nM in adipocytes. In addition, 25f has 94% oral bioavailability in rat and >1000× selectivity over 11β-HSD2. In mice, 25f was distributed to the target tissues

  基于结构的设计直接导致了1,3-恶二酮-2-酮9a在体外对11β-HSD1的IC 50为42 nM。优化9a以提高体外酶和细胞效能可得到25f，其酶的IC 50值为0.8 nM，而在脂肪细胞中的IC 50值为2.5 nM。另外，25f在大鼠中具有94％的口服生物利用度，并且相对于11β-HSD2具有> 1000倍的选择性。在小鼠中，将25f分配至靶组织，肝脏和脂肪，在食蟹猴中，口服10 mg / kg剂量的可的松攻击后，皮质醇的产生减少了85％。