(R,R)-trans-2-phenyl-cyclopropane-1-carboxylic acid benzyl ester | 573968-14-6

• 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: (R,R)-trans-2-phenyl-cyclopropane-1-carboxylic acid benzyl ester
• 英文别名: benzyl (1R,2R)-2-phenylcyclopropane-1-carboxylate
• CAS: 573968-14-6
• 化学式: C₁₇H₁₆O₂
• 分子量: 252.313
• InChiKey: NYBWCLCZSJXDGH-JKSUJKDBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  19
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (R,R)-trans-2-phenyl-cyclopropane-1-carboxylic acid benzyl ester 在 sodium hydroxide 、 水 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (1R,2R)-trans-2-phenyl-1-cyclopropanecarboxylic acid
  参考文献：
  名称：

  Stereoselective palladium-catalyzed cyclopropanation of α,β-unsaturated carboxylic acids derivatized with oppolzer's sultam

  摘要：

  N-enoyl sultams, derived from alpha,beta-unsaturated carboxylic acids and bornane[10,2]sultam, undergo a stereoselective Pd-catalyzed cyclopropanation upon treatment with diazomethane. The stereoselectivity of the reaction is temperature dependent.

  DOI：

  10.1016/0040-4039(91)80102-c
• 作为产物：
  描述：

  [(1S,5S,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-azatricyclo[5.2.1.01,5]decan-4-yl]-[(1R,2R)-2-phenylcyclopropyl]methanone 、 苯甲醇 在 titanium(IV) isopropylate 作用下， 生成 (R,R)-trans-2-phenyl-cyclopropane-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Stereoselective palladium-catalyzed cyclopropanation of α,β-unsaturated carboxylic acids derivatized with oppolzer's sultam

  摘要：

  N-enoyl sultams, derived from alpha,beta-unsaturated carboxylic acids and bornane[10,2]sultam, undergo a stereoselective Pd-catalyzed cyclopropanation upon treatment with diazomethane. The stereoselectivity of the reaction is temperature dependent.

  DOI：

  10.1016/0040-4039(91)80102-c

文献信息

• A de novo peroxidase is also a promiscuous yet stereoselective carbene transferase
  作者：Richard Stenner、Jack W. Steventon、Annela Seddon、J. L. Ross Anderson

  DOI：10.1073/pnas.1915054117

  日期：2020.1.21

  activity extends to the efficient and stereoselective intermolecular transfer of carbenes to olefins, heterocycles, aldehydes, and amines. Not only is this a report of carbene transferase activity in a completely de novo protein, but also of enzyme-catalyzed ring expansion of aromatic heterocycles via carbene transfer by any enzyme.

  通过构建体内组装的、催化能力强的过氧化物酶 C45，我们最近证明了简单的、从头设计的血红素蛋白的催化潜力。在这里，我们展示了 C45 的酶活性延伸到卡宾到烯烃、杂环、醛和胺的高效和立体选择性分子间转移。这不仅是关于完全从头蛋白质中卡宾转移酶活性的报告，而且是通过任何酶的卡宾转移酶催化芳族杂环扩环的报告。
• Synthesis of a New Chiral Nonracemic <i>C</i>₂-Symmetric 2,2‘-Bipyridyl Ligand and Its Application in Copper(I)-Catalyzed Enantioselective Cyclopropanation Reactions
  作者：Michael P. A. Lyle、Peter D. Wilson

  DOI：10.1021/ol049853c

  日期：2004.3.1

  synthesis of a low molecular weight, chiral nonracemic and C(2)-symmetric bipyridyl ligand is reported. The ligand was prepared using a catalytic asymmetric dihydroxylation reaction of a pyrindine as a key step. The ligand was evaluated in the asymmetric copper(I)-catalyzed cyclopropanation reactions of a series of alkenes and diazoesters. Very high diastereoselectivities and enantioselectivities were

  低分子量，手性非外消旋和C（2）对称联吡啶配体的有效合成的报告。配体是使用嘧啶的催化不对称二羟基化反应作为关键步骤制备的。在一系列烯烃和重氮酯的不对称铜（I）催化的环丙烷化反应中评估了配体。观察到非常高的非对映选择性和对映选择性（> 95：5 dr和高达99％ee）。这些是手性联吡啶配体的最高立体选择性。[结构：见文字]
• A Practical and Controllable Enantioselective Synthesis of 2-Phenyl-1-cyclopropanecarboxylates via a Camphor-Derived Sulfonium Ylide
  作者：Zhi-Zhen Huang、Kun Huang

  DOI：10.1055/s-2005-869852

  日期：——

  We have developed a practical and controllable enantio­selective synthesis of 2-phenyl-1-cyclopropane-carboxylates via camphor-derived sulfonium ylide. The procedure has many advantages such as cheap starting materials, facile synthetic procedures, good yields, excellent diastereoselectivities and high enantioselectivities.

  我们开发出了一种通过樟脑衍生的醯化锍对 2-苯基-1-环丙烷羧酸酯进行对映选择性合成的实用可控方法。该方法具有许多优点，如起始原料便宜、合成过程简便、产率高、非对映选择性好和对映选择性高。
• Stereoselective palladium-catalyzed cyclopropanation of α,β-unsaturated carboxylic acids derivatized with oppolzer's sultam
  作者：Jerk Vallg»rda、Uli Hacksell

  DOI：10.1016/0040-4039(91)80102-c

  日期：1991.9

  N-enoyl sultams, derived from alpha,beta-unsaturated carboxylic acids and bornane[10,2]sultam, undergo a stereoselective Pd-catalyzed cyclopropanation upon treatment with diazomethane. The stereoselectivity of the reaction is temperature dependent.