(1R,2S)-cis-1-(Hydroxymethyl)-2-(3'-phenylpropyl)cyclopropane | 139400-23-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (1R,2S)-cis-1-(Hydroxymethyl)-2-(3'-phenylpropyl)cyclopropane
• 英文别名: (1R,2S)-1-(Hydroxymethyl)-2-(3-phenyl-1-propyl)cyclopropane；cis-1-hydroxymethyl-2-(3-phenyl-propyl)cyclopropane；[(1R,2S)-2-(3-phenylpropyl)cyclopropyl]methanol
• CAS: 139400-23-0
• 化学式: C₁₃H₁₈O
• 分子量: 190.285
• InChiKey: JKVNOHPIYDSIQA-STQMWFEESA-N

物化性质

• 沸点：
  299.5±9.0 °C(Predicted)
• 密度：
  1.019±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.64
• 重原子数：
  14.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  20.23
• 氢给体数：
  1.0
• 氢受体数：
  1.0

反应信息

• 作为产物：
  描述：

  6-苯基己-2-炔-1-醇 在 Lindlar catalyst 硝酸铵 、 sodium tetrahydroborate 、 氢气 、 diethylzinc 、 4-甲基苯磺酸吡啶 、 溶剂黄146 、 pyridinium chlorochromate 作用下， 以 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 、 苯 为溶剂， 反应 35.25h， 生成 (1R,2S)-cis-1-(Hydroxymethyl)-2-(3'-phenylpropyl)cyclopropane
  参考文献：
  名称：

  Asymmetric Cyclopropanation Using New Chiral Auxiliaries Derived from D-Fructose

  摘要：

  Acetals of alpha,beta-unsaturated aldehydes with 3-O-alkylated derivatives of 1,2-O-isopropylidene-beta-D-fructopyranose and 1,2-O-isopropylidene-beta-D-psicopyranose, which are readily available from D-fructose, were cyclopropanated with Et(2)Zn and CH2I2 with good diastereoselectivity. The effects of structure of the acetals on enantioselectivity were examined.

  DOI：

  10.1021/jo00108a018

文献信息

• Enantioselective Construction of Cyclopropane Rings via Asymmetric Simmons-Smith Reaction of Allylic Alcohols.
  作者：Yutaka Ukaji、Mitsuhiro Nishimura、Tamotsu Fujisawa

  DOI：10.1246/cl.1992.61

  日期：——

  The Simmons-Smith reaction starting from allylic alcohols using (R,R)-diethyl tartrate as a chiral auxiliary was found to proceed enantioselectively; i.e., the treatment of allylic allylic alcohols with diethylzinc and diethyl tartrate, followed by the reaction with diethylzinc and diiodomethane, afforded the corresponding cyclopropylmethyl alcohols in optically active form

  发现以 (R,R)-酒石酸二乙酯为手性助剂，以烯丙醇为原料的 Simmons-Smith 反应对映选择性进行；即，用二乙基锌和酒石酸二乙酯处理烯丙醇，然后与二乙基锌和二碘甲烷反应，得到相应的旋光形式的环丙基甲醇
• Synthesis of optically active cis- and trans-1,2-disubstituted cyclopropane derivatives by the Simmons-Smith reaction of allyl alcohol derivatives derived from (R)-2,3-O-isopropylideneglyceraldehyde
  作者：Tsutomu Morikawa、Hirofumi Sasaki、Ryo Hanai、Akira Shibuya、Takeo Taguchi

  DOI：10.1021/jo00080a017

  日期：1994.1

  The Simmons-Smith reactions of Z- and E-allyl alcohol derivatives 6 derived from (R)-2,3-O-isopropylideneglyceraldehyde (5) were used for the synthesis of optically active cis- and trans-1,2 disubstituted cyclopropane derivatives. Reaction of 6 with diethyl zinc and diiodomethane gave cyclopropane derivatives 7 in 84% to quantitative yields with 35 to approximate to 100% des. Identical facial selectivities toward the double bonds, Ire-asi for Z-6 and 1re-2re for E-6, were observed in the cyclopropanations. The diastereoselectivity was dependent on the protecting group on the terminal allylic oxygen (R of 6, TBDPS > MOM > Bn) and on the stereochemistry of the double bond (Z > E). For TBDPS ethers Z- and E-6c, cis- and trans-7c were obtained as single diastereomers respectively. It was clearly demonstrated that the stereoselectivity of the cyclopropanation is controlled by the directing effect of the allylic oxygen (O-1) of the dioxolane ring which coordinates to the reagent. The terminal allylic oxygen (O-2) lowered the diastereoselectivity This reaction was applied to the synthesis of optically active cyclopropane analogs of gamma-aminobutyric acid (GABA) 18, 22, and ent-22.