1-(methoxycarbonyl)-2-(phenylmethylene)cyclopropanecarboxylic acid methyl ester | 866412-83-1

• 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: 1-(methoxycarbonyl)-2-(phenylmethylene)cyclopropanecarboxylic acid methyl ester
• 英文别名: (E)-dimethyl 2-benzylidenecyclopropane-1,1-dicarboxylate；dimethyl (E)-2-benzylidenecyclopropane-1,1-dicarboxylate；dimethyl (2E)-2-benzylidenecyclopropane-1,1-dicarboxylate
• CAS: 866412-83-1
• 化学式: C₁₄H₁₄O₄
• 分子量: 246.263
• InChiKey: BCMLXNVHPNVCPD-DHZHZOJOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(methoxycarbonyl)-2-(phenylmethylene)cyclopropanecarboxylic acid methyl ester 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.3h， 以72%的产率得到(Z)-dimethyl 2-(3-phenylallylidene)malonate
  参考文献：
  名称：

  AnBuLi 介导的（芳基亚甲基）环丙烷-1,1-二羧酸酯的快速立体选择性开环重排

  摘要：

  我们在此报告了（芳基亚甲基）环丙烷 1,1-二酯的 nBuLi 介导的、快速的开环重排，以制备具有良好立体选择性的 1,3-二烯衍生物。还讨论了反应机理。

  DOI：

  10.1002/ejoc.200901165
• 作为产物：
  描述：

  dimethyl 2-benzylcycloprop-2-ene-1,1-dicarboxylate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以89%的产率得到1-(methoxycarbonyl)-2-(phenylmethylene)cyclopropanecarboxylic acid methyl ester
  参考文献：
  名称：

  DBU-mediated transformation of arylmethylenecyclopropenes to alkylidenecyclopropanes

  摘要：

  An interesting DBU-mediated intramolecular isomerization of arylmethylenecyclopropenes 1 to alkylidenecyclopropanes (ACPs) has been described in this context. A variety of ACPs were obtained through a base-assisted manner in moderate to good yields under mild conditions with good stereoselectivities in most cases. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.04.076

文献信息

• Lewis acid-catalyzed nucleophilic ring-opening/intramolecular Conia-ene reactions of methylenecyclopropane 1,1-diesters with propargyl alcohols
  作者：Bao Hu、Jun Ren、Zhongwen Wang

  DOI：10.1016/j.tet.2010.11.048

  日期：2011.1

  Lewis acid-catalyzed nucleophilic ring opening of methylenecyclopropane (MCP) 1,1-diesters with propargyl alcohols. Unlike the proximal-bond cleavage mode observed in cases of unactivated MCPs, the intrinsic characteristic of MCP 1,1-diesters gave a regiospecific distal-bond cleavage under attack of propargyl alcohols as nucleophiles. By combining a subsequent intramolecular Conia-ene reaction, 3,5

  我们提出了路易斯酸催化的炔丙基醇与亚甲基环丙烷（MCP）1,1-二酯的亲核开环。与未激活的MCP情况下观察到的近端键裂解模式不同，MCP 1,1-二酯的内在特征在炔丙醇作为亲核试剂的攻击下产生了区域特异性的远端键裂解。通过结合随后的分子内Conia-ene反应，可以逐步或一锅法获得3,5-二亚甲基四氢吡喃。
• Catalytic, Formal Homo-Nazarov-Type Cyclizations of Alkylidene Cyclopropane-1,1-Ketoesters: Access to Functionalized Arenes and Heteroaromatics
  作者：Joel Aponte-Guzmán、J. Evans Taylor、Elayna Tillman、Stefan France

  DOI：10.1021/ol501676q

  日期：2014.7.18

  A catalytic, formal homo-Nazarov-type cyclization of alkylidene cyclopropanes (ACPs) to give functionalized arenes and heteroaromatics is reported. In the presence of a Lewis acid catalyst, the ACP 1,1-ketoesters undergo distal bond cleavage to afford an allyl cation intermediate. Adjacent m-attack on the ally! cation then provides a six-membered ring that undergoes rapid aromatization. In these cases, benzenoid products are formed in up to 98% yield. Strategic choice of the substitution about the ACP allows for the generation of other useful isomeric products in good yields.
• An Efficient Stereoselective Synthesis of 4,5-<i>trans</i>-1,5-<i>cis</i>-3-Oxabicyclo[3.1.0]hexan-2-ones via the Iodolactonization of Alkylidenecyclopropyl Esters
  作者：Shengming Ma、Lianghua Lu

  DOI：10.1021/jo050878e

  日期：2005.9.1

  A highly stereoselective iodolactonization of alkylidenecyclopropyl esters with iodine or N-iodosuccinimide (NIS) in aqueous CH3CN to afford 4,5-trans-1,5-cis-3-oxabicyclo-[3.1.0]hexane-2ones is described. The reaction is very general, accommodating a wide range of substituents. A plausible mechanism that explains the essential role of water in this reaction is proposed.
• Intermolecular Tandem Addition−Cyclization of Bromoallenes:  A Facile Synthesis of Methylenecyclopropyl Carboxylates and Polysubstituted Furans
  作者：Lubin Xu、Xian Huang、Fangrui Zhong

  DOI：10.1021/ol061993u

  日期：2006.10.1

  The base-mediated reactions of 1,3-dicarbonyl compounds with bromoallenes used as an allyl dication equivalent were explored. The corresponding dimethyl methylenecyclopropane-1,1-dicarboxylates and 2,3,4-trisubstituted furans were efficiently synthesized.
• DBU-mediated transformation of arylmethylenecyclopropenes to alkylidenecyclopropanes
  作者：Rui Sang、Hai-Bin Yang、Min Shi

  DOI：10.1016/j.tetlet.2013.04.076

  日期：2013.7

  An interesting DBU-mediated intramolecular isomerization of arylmethylenecyclopropenes 1 to alkylidenecyclopropanes (ACPs) has been described in this context. A variety of ACPs were obtained through a base-assisted manner in moderate to good yields under mild conditions with good stereoselectivities in most cases. (C) 2013 Elsevier Ltd. All rights reserved.