phenyl 2-phenylcyclopropanecarboxylate | 86597-63-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚酯
• 英文名称: phenyl 2-phenylcyclopropanecarboxylate
• 英文别名: Cyclopropanecarboxylic acid, trans-2-phenyl-, phenyl ester；phenyl 2-phenylcyclopropane-1-carboxylate
• CAS: 86597-63-9
• 化学式: C₁₆H₁₄O₂
• 分子量: 238.286
• InChiKey: RFWVVXSKWXDEGN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  18
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (2,2-二溴环丙基)苯 、 苯酚 以57%的产率得到
  参考文献：
  名称：

  HIRAO TOSHIKAZU; HARANO YOSHIYUKI; YAMANA YOSHIHIRO; HAMADA YUJI; NAGATA +, BULL. CHEM. SOC. JAP., 59,(1986) N 5, 1341-1347

  摘要：

  DOI：
• 作为试剂：
  描述：

  3-戊酮 在 四氯化钛 、 phenyl 2-phenylcyclopropanecarboxylate 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以92%的产率得到5-乙基-5-羟基-4-甲基庚烷-3-酮
  参考文献：
  名称：

  SmI₂-Promoted Reformatsky-Type Reaction and Acylation of Alkyl 1-Chlorocyclopropanecarboxylates

  摘要：

  In the presence of HMPA in THF, highly stereoselective Sml(2)-promoted substitutions of alkyl 1-chlorocyclopropanecarboxylates 1 using various ketones, aldehydes (Reformatsky-type reaction), and acyl chlorides (acylation) proceeded to give trans-adducts (2 or 5) in good to high yield with excellent trans-stereoselectivity (trans-add/cis-add = > 99/1). The Reformatsky-type reaction of 1 with aldehydes and unsymmetrical ketones proceeded with moderate diastereoselectivity (re-face-adduct/si-face-adduct = 60/40-75/25).

  DOI：

  10.1021/ol8022038

文献信息

• Nickel‐Catalyzed Asymmetric Hydroaryloxy‐ and Hydroalkoxycarbonylation of Cyclopropenes
  作者：Rongrong Yu、Song‐Zhou Cai、Can Li、Xianjie Fang

  DOI：10.1002/anie.202200733

  日期：2022.9.5

  Highly enantioselective inter- and intramolecular Ni-catalyzed hydroalkoxycarbonylation yields various enantioenriched polysubstituted cyclopropanecarboxylic derivatives with quaternary carbon stereocenters.

  高度对映选择性的分子间和分子内 Ni 催化的氢化烷氧基羰基化产生各种具有季碳立体中心的对映富集的多取代环丙烷羧酸衍生物。
• Nucleophilic Carbenes Derived from Dichloromethane
  作者：Mingxin Liu、Nguyen Le、Christopher Uyeda

  DOI：10.1002/anie.202308913

  日期：2023.10.16

  Nickel catalysts promote cyclopropanation reactions of electron-deficient alkenes using dichloromethane as a methylene source. An asymmetric variant using a chiral pyridine-bis(oxazoline) ligand provides access to pharmaceutically relevant 2-aryl cyclopropyl carboxylates in highly enantioenriched form. The proposed mechanism involves the formation of a nucleophilic nickel carbene that reacts by a

  镍催化剂使用二氯甲烷作为亚甲基源，促进缺电子烯烃的环丙烷化反应。使用手性吡啶-双（恶唑啉）配体的不对称变体提供了高度对映体富集形式的药学相关的 2-芳基环丙基羧酸盐。所提出的机制涉及形成亲核镍卡宾，该卡宾通过 [2+2] -环加成/C-C 还原消除途径反应。
• Tetracarbonyl nickel induced reaction of gem-dibromocyclopropanes with alcohols or amines.
  作者：Toshikazu Hirao、Yoshiyuki Harano、Yoshihiro Yamana、Yoshiki Ohshiro、Toshio Agawa

  DOI：10.1016/s0040-4039(00)81628-7

  日期：1983.1
• Bis(oxazoline)·copper(I)-catalyzed enantioselective cyclopropanation of cinnamate esters with diazomethane
  作者：André B. Charette、Marc K. Janes、Hélène Lebel

  DOI：10.1016/s0957-4166(03)00076-4

  日期：2003.4

  Chiral bis(oxazoline)-copper(l) complexes were found to be effective catalysts for the enantioselective cyclopropanation reaction of trans-cinnamate esters exploiting an argon flow mediated diazomethane addition method. After optimization of the catalyst structure, good yields and enantiomeric excesses were obtained with electron-poor methyl cinnamate derivatives. Sterically demanding esters gave lower yields and enantioselectivities. The correlation between the product enantiopurities and the sigma(+) values of the aromatic para-substituents was shown to be linear in a Hammet-type plot. (C) 2003 Elsevier Science Ltd. All rights reserved.
• HIRAO, TOSHIKAZU;HARANO, YOSHIYUKI;YAMANA, YOSHIHIRO;OHSHIRO, YOSHIKI;AGA+, TETRAHEDRON LETT., 1983, 24, N 12, 1255-1258
  作者：HIRAO, TOSHIKAZU、HARANO, YOSHIYUKI、YAMANA, YOSHIHIRO、OHSHIRO, YOSHIKI、AGA+

  DOI：——

  日期：——