3-((1S,2S)-2-heptylcycloprop-1-yl)propionic acid | 666822-26-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-((1S,2S)-2-heptylcycloprop-1-yl)propionic acid
• 英文别名: 3-[(1S,2S)-2-heptylcyclopropyl]propionic acid；3-[(1S,2S)-2-heptylcyclopropyl]propanoic acid
• CAS: 666822-26-0
• 化学式: C₁₃H₂₄O₂
• 分子量: 212.332
• InChiKey: RLZULRFRISISCU-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  15
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  37.3
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-((1S,2S)-2-heptylcycloprop-1-yl)propionic acid 在 氯化亚砜 作用下， 反应 2.0h， 生成 3-((1S,2S)-2-heptylcycloprop-1-yl)propionyl chloride
  参考文献：
  名称：

  The absolute stereochemistry of grenadamide

  摘要：

  3-(2S-Heptylcycloprop-1S-yl)propanoic acid 2-phenylethanamide was synthesised from cis-cyclopropan-1,2-dimethanol via enzymatic desymmetrisation of the dibutyrate; it gave identical NMR spectroscopic data to those reported for grenadamide but had an equal and opposite absolute rotation, indicating that the latter is the 2R,1R-enantiomer. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.006
• 作为产物：
  描述：

  (E)-3-((1S,2S)-2-heptylcycloprop-1-yl)acrylic acid ethyl ester 在 氢氧化钾 、 potassium diazodicarboxylate 、 溶剂黄146 作用下， 以 甲醇 、 乙醇 、 水 为溶剂， 反应 49.0h， 生成 3-((1S,2S)-2-heptylcycloprop-1-yl)propionic acid
  参考文献：
  名称：

  The absolute stereochemistry of grenadamide

  摘要：

  3-(2S-Heptylcycloprop-1S-yl)propanoic acid 2-phenylethanamide was synthesised from cis-cyclopropan-1,2-dimethanol via enzymatic desymmetrisation of the dibutyrate; it gave identical NMR spectroscopic data to those reported for grenadamide but had an equal and opposite absolute rotation, indicating that the latter is the 2R,1R-enantiomer. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2003.11.006

文献信息

• Carbohydrate-Derived Bis(oxazoline) Ligand in the Total Synthesis of Grenadamide
  作者：Mike Boysen、Tobias Minuth

  DOI：10.1055/s-0030-1258143

  日期：2010.8

  Using an optimised carbohydrate-based bis(oxazoline) ligand and copper(I) triflate, unactivated aliphatic alkenes were cyclopropanated­ with simple ethyl diazoacetate, giving the corresponding products in good yields and high stereoselectivities. The trans-disubstituted cyclopropyl carboxylic acid ester derived from 1-nonene was subsequently used as the key intermediate for the synthesis of the (+)-enantiomer

  使用优化的基于碳水化合物的双（恶唑啉）配体和三氟甲磺酸铜（I），将未活化的脂肪族烯烃与简单的重氮乙酸乙酯进行环丙烷化反应，从而以高收率和高立体选择性得到相应的产物。随后将衍生自1-壬烯的反式-二取代的环丙基羧酸酯用作合成天然产物（-）-石榴糖酰胺的（+）-对映异构体的关键中间体。本文报道的对格林纳酰胺的高效且高产率的方法是第一个利用不对称环丙烷化来构建手性环丙基单元的方法。 碳水化合物-配体设计-不对称催化-天然产物-环丙烷化
• The absolute stereochemistry of grenadamide
  作者：Juma'a R. Al Dulayymi、Mark S. Baird、Keith Jones

  DOI：10.1016/j.tet.2003.11.006

  日期：2004.1

  3-(2S-Heptylcycloprop-1S-yl)propanoic acid 2-phenylethanamide was synthesised from cis-cyclopropan-1,2-dimethanol via enzymatic desymmetrisation of the dibutyrate; it gave identical NMR spectroscopic data to those reported for grenadamide but had an equal and opposite absolute rotation, indicating that the latter is the 2R,1R-enantiomer. (C) 2003 Elsevier Ltd. All rights reserved.