(E)-1-苯乙烯环丙烷胺 | 604799-99-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: (E)-1-苯乙烯环丙烷胺
• 英文名称: 1-(2-phenylvinyl)cyclopropylamine
• 英文别名: 1-styrylcyclopropanamine；(E)-1-Styrylcyclopropanamine；1-[(E)-2-phenylethenyl]cyclopropan-1-amine
• CAS: 604799-99-7
• 化学式: C₁₁H₁₃N
• 分子量: 159.231
• InChiKey: SRQFAPCKOFPXIZ-VOTSOKGWSA-N

物化性质

• 沸点：
  253.7±19.0 °C(Predicted)
• 密度：
  1.159±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (E)-1-苯乙烯环丙烷胺 在 3 A molecular sieve 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 6.0h， 生成 2-phenyl-5-styryl-3,4-dihydro-2H-pyrrole
  参考文献：
  名称：

  The N-Cyclopropylimine-1-pyrroline Photorearrangement as a Synthetic Tool:  Scope and Limitations

  摘要：

  [GRAPHICS]The scope and limitations of the photorearrangement of N-cyclopropylimines to 1-pyrrolines are presented. The influence on the reactivity of different substituents throughout the cyclopropane ring and at the iminic position of the N-cyclopropylimine structure is discussed. The observed effects are interpreted from computational studies. The principal findings relate to (1) the enhanced reactivity of 1-substituted compounds toward rearrangement, (2) the lack of reactivity of crowded cyclopropanes, and (3) the high chemoselectivity of the process.

  DOI：

  10.1021/jo050871x
• 作为产物：
  描述：

  (E)-1-(1-styryl)-1-(tosyloxy)cyclopropane 在 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 1,3-丙二硫醇 、 sodium azide 、 15-冠醚-5 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 生成 (E)-1-苯乙烯环丙烷胺
  参考文献：
  名称：

  Regioselective palladium (O) catalyzed azidation and amination of 1-alkenylcyclpropyl esters: a new route to 2,3-methanoamino acids.

  摘要：

  Palladium (0) catalyzed azidation of 1-alkenylcyclopropyl esters provides regioselectively 1-azido-1-alkenyl cyclopropanes, convenient precursors of 2,3-methanoamino acids. On the other hand, amination occurred exclusively on the less substituted allylic end, providing strained 2-cyclopropylideneethylamine derivatives.

  DOI：

  10.1016/s0040-4039(00)60525-7

文献信息

• A Direct Synthesis of 1-Aryl- and 1-Alkenylcyclopropylamines from Aryl and Alkenyl Nitriles
  作者：Philippe Bertus、Jan Szymoniak

  DOI：10.1021/jo034710+

  日期：2003.9.1

  The reaction of various aromatic nitriles with 1.1 equiv of Ti(Oi-Pr)(4) and 2.2 equiv of EtMgBr followed by addition of a Lewis acid gave 1-aryl cyclopropylamines in 43-76% yields. Under similar conditions, conjugated alkenenitriles afford 1-alkenylcyclopropylamines (42-65%).

  各种芳族腈与1.1当量的Ti（Oi-Pr）（4）和2.2当量的EtMgBr的反应，然后加入路易斯酸，以43-76％的收率得到1-芳基环丙胺。在类似条件下，共轭烯腈提供1-烯基环丙胺（42-65％）。
• LSD1 INHIBITORS AND USES THEREOF
  申请人：Constellation Pharmaceuticals, Inc.

  公开号：US20180290976A1

  公开（公告）日：2018-10-11

  Provided are novel compounds of Formula (I): and pharmaceutically acceptable salts thereof, which are useful for treating a variety of diseases, disorders or conditions, associated with LSD1. Also provided are pharmaceutical compositions comprising the novel compounds of Formula (I), pharmaceutically acceptable salts thereof, and methods for their use in treating one or more diseases, disorders or conditions, associated with LSD1.
• The <i>N</i>-Cyclopropylimine-1-pyrroline Photorearrangement as a Synthetic Tool:  Scope and Limitations
  作者：Alberto Soldevilla、Diego Sampedro、Pedro J. Campos、Miguel A. Rodríguez

  DOI：10.1021/jo050871x

  日期：2005.8.1

  [GRAPHICS]The scope and limitations of the photorearrangement of N-cyclopropylimines to 1-pyrrolines are presented. The influence on the reactivity of different substituents throughout the cyclopropane ring and at the iminic position of the N-cyclopropylimine structure is discussed. The observed effects are interpreted from computational studies. The principal findings relate to (1) the enhanced reactivity of 1-substituted compounds toward rearrangement, (2) the lack of reactivity of crowded cyclopropanes, and (3) the high chemoselectivity of the process.
• Regioselective palladium (O) catalyzed azidation and amination of 1-alkenylcyclpropyl esters: a new route to 2,3-methanoamino acids.
  作者：Pierre Aufranc、Jean Ollivier、Andreas Stolle、Claudia Bremer、Mazen Es-Sayed、Armin de Meijere、Jacques Salaün

  DOI：10.1016/s0040-4039(00)60525-7

  日期：1993.6

  Palladium (0) catalyzed azidation of 1-alkenylcyclopropyl esters provides regioselectively 1-azido-1-alkenyl cyclopropanes, convenient precursors of 2,3-methanoamino acids. On the other hand, amination occurred exclusively on the less substituted allylic end, providing strained 2-cyclopropylideneethylamine derivatives.