Methyl 2-<1-(diphenylmethylene)aminocyclopropyl>-2-chloroacetate | 125506-36-7

• 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: Methyl 2-<1-(diphenylmethylene)aminocyclopropyl>-2-chloroacetate
• 英文别名: Methyl 2-chloro-2-(1-(diphenylmethyleneamino)cyclopropyl)acetate；methyl 2-[1-(benzhydrylideneamino)cyclopropyl]-2-chloroacetate
• CAS: 125506-36-7
• 化学式: C₁₉H₁₈ClNO₂
• 分子量: 327.81
• InChiKey: VQJISNKVVQTNDT-UHFFFAOYSA-N

物化性质

• 熔点：
  64 °C(Solv: hexane (110-54-3); ethyl ether (60-29-7))
• 沸点：
  422.5±31.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  38.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  Methyl 2-<1-(diphenylmethylene)aminocyclopropyl>-2-chloroacetate 在 三乙胺 、 lithium iodide 作用下， 以 异丙醇 为溶剂， 反应 168.0h， 以73%的产率得到2-((二苯基亚甲基)氨基)环丁烯羧酸甲酯
  参考文献：
  名称：

  Cyclopropyl building blocks for organic synthesis. Part 22. Facile synthesis of stable analogs of 2-oxocyclobutanecarboxylates: 2-[(diphenylmethylene)amino]cyclobutenecarboxylates, derivatives and reactions

  摘要：

  An efficient two-step synthesis of 2-[(diphenylmethylene)amino]cyclobutenecarboxylate (4a) and some analogous derivatives from 2-chloro-2-cyclopropylideneacetates 2, 17, 22, and 25 and nonenolizable ketimines, especially diphenylmethyleneamine (DPMA-H), is described. A likely mechanism for the formation of 4a from the primary Michael adduct 3 of DPMA-H to 2 and its substituted analogues is presented. The unique neighboring group effect of the DPMA moiety to allow formation of an azaspiropentane intermediate and its regioselective rearrangement to cyclobutenamine derivatives is discussed and further exemplified by an extremely facile SET alpha-chlorination. Compound 4a and derivatives undergo a thermal ring-opening reaction to the corresponding butadienes with subsequent formation of 1,3-disubstituted 3,4-dihydroisoquinolines 39. Further transformations of 4a and some derivatives include transesterification, hydrolysis to methyl 2-oxocyclobutanecarboxylates, and addition of N-phenyltriazolinedione.

  DOI：

  10.1021/jo00075a047
• 作为产物：
  描述：

  二苯甲酮亚胺 、 2-氯-2-环丙基亚甲基乙酸甲酯 以 甲醇 为溶剂， 反应 24.0h， 以100%的产率得到Methyl 2-<1-(diphenylmethylene)aminocyclopropyl>-2-chloroacetate
  参考文献：
  名称：

  异喹啉-4-羧酸和2-氮杂-3,3a-二氢azulene-3a-羧酸衍生物的短合成新方法

  摘要：

  环亚丙基乙酸酯（2a，b）与（二苯基亚甲基）胺（DPMA-H）（1）进行正式的[2 + 4]环加成反应生成二氢-1-苯基异喹啉-4-羧酸酯（8a）和1-苯基异喹啉-4-羧酸酯（7b）；另一方面，在碱性条件下，将DPMA-H在（2b）上的迈克尔加成产物仅得到1-苯基-2-氮杂-azulene-3a-羧酸盐（12）。

  DOI：

  10.1039/c39900000574

文献信息

• 1,4-Addition of (Diphenylmethylene)amine to Acceptor Substituted Olefins. A Versatile Synthesis of Protected β-Amino Acids, Nitriles, and Ketones
  作者：Ludger Wessjohann、Gregory Mcgaffin、Armin de Meijere

  DOI：10.1055/s-1989-27252

  日期：——

  (Diphenylmethylene)amine [benzophenone imine, DPMA-H] cleanly reacts with a variety of α,β-unsaturated esters, nitriles, ketones, and aldehydes 1a-q to give Michael type adducts 2a-q, generally, in respectable to excellent yields. Sterically congested and donor-substituted Michael acceptors do not react. The β-amino-substituted products can be further transformed in their protected form, or selectively deprotected under mild conditions, e.g. by catalytic hydrogenation.

  (二苯基亚甲基)胺[二苯甲酮亚胺，DPMA-H]能与多种δ、δ-不饱和酯、腈、酮和醛 1a-q 顺利反应，生成迈克尔型加合物 2a-q，收率一般可观，甚至极佳。立体拥塞和供体取代的迈克尔受体不会发生反应。δ-氨基取代的产物可以被保护的形式进一步转化，或在温和的条件下选择性地脱保护，例如通过催化氢化。
• New short syntheses of isoquinoline-4-carboxylic acid and 2-aza-3,3a-dihydroazulene-3a-carboxylic acid derivatives
  作者：Ludger Wessjohann、Lars Skattebøl、Armin De Meijere

  DOI：10.1039/c39900000574

  日期：——

  Cyclopropylideneacetates (2a,b) undergo a formal [2 + 4] cycloaddition with (diphenylmethylene)amine (DPMA-H)(1) to yield dihydro-1-phenylisoquinoline-4-carboxylate (8a) and 1-phenylisoquinoline-4-carboxylate (7b); the Michael adduct of DPMA-H onto (2b), on the other hand, under basic conditions gives 1-phenyl-2-aza-azulene-3a-carboxylate (12) exclusively.

  环亚丙基乙酸酯（2a，b）与（二苯基亚甲基）胺（DPMA-H）（1）进行正式的[2 + 4]环加成反应生成二氢-1-苯基异喹啉-4-羧酸酯（8a）和1-苯基异喹啉-4-羧酸酯（7b）；另一方面，在碱性条件下，将DPMA-H在（2b）上的迈克尔加成产物仅得到1-苯基-2-氮杂-azulene-3a-羧酸盐（12）。
• ANTIBACTERIAL AGENTS
  申请人：Moser Heinz E.

  公开号：US20100190766A1

  公开（公告）日：2010-07-29

  Antibacterial compounds of formula (I) are provided: as well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.

  提供化学式(I)的抗菌化合物：以及其立体异构体，药学上可接受的盐，酯和前药；包含这些化合物的制药组合物；通过给予这些化合物的途径治疗细菌感染的方法；以及制备这些化合物的过程。
• Antibacterial agents
  申请人：Achaogen, Inc.

  公开号：EP2662353A2

  公开（公告）日：2013-11-13

  Antibacterial compounds of formula (I) are provided, as well as stereoisomers, pharmaceutically acceptable salts, esters, and prodrugs thereof; pharmaceutical compositions comprising such compounds; methods of treating bacterial infections by the administration of such compounds; and processes for the preparation of such compounds.

  提供了式 (I) 的抗菌化合物及其立体异构体、药学上可接受的盐、酯和原药；包含此类化合物的药物组合物；通过服用此类化合物治疗细菌感染的方法；以及制备此类化合物的工艺。
• WESSJOHANN, LUDGER;MCGAFFIN, GREGORY;MEIJERE, ARMIN DE, SYNTHESIS,(1989) N, C. 359-363
  作者：WESSJOHANN, LUDGER、MCGAFFIN, GREGORY、MEIJERE, ARMIN DE

  DOI：——

  日期：——