(S)-(-)-1-(ethylideneamino)-2-(methoxymethyl)pyrrolidine | 107985-85-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯烷类
• 英文名称: (S)-(-)-1-(ethylideneamino)-2-(methoxymethyl)pyrrolidine
• 英文别名: (-)-(S)-1-ethylideneamino-2-(methoxymethyl)pyrrolidine；(E)-N-[(2S)-2-(methoxymethyl)pyrrolidin-1-yl]ethanimine
• CAS: 107985-85-3
• 化学式: C₈H₁₆N₂O
• 分子量: 156.228
• InChiKey: NENOKYKTBCTASZ-FVKOELHVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (S)-(-)-1-(ethylideneamino)-2-(methoxymethyl)pyrrolidine 在 lithium diisopropyl amide 作用下， 反应 8.5h， 生成 (S,R)-2-methoxymethyl-1-(2-methylthio-1-pentylidenamino)-pyrrolidine
  参考文献：
  名称：

  Enantioselective synthesis of 2-sulfenylated aldehydes: Alkylation of sulfenylated acetaldehyde SAMP-hydrazones

  摘要：

  A practical and efficient enantioselective synthesis of 2-sulfenylated aldehydes (S)-6 is described, based on the alpha-alkylation of sulfenylated acetaldehyde SAMP hydrazones (S)-4, easily prepared from bromoacetaldehyde diethyiacetal 1, thiols and (S)-1-amino-2-methoxymethyl-pyrrolidine (SAMP). A chemoselective oxidative cleavage of the intermediate SAMP hydrazones (S,S)-5 with ozone gives rise to the title compounds (S)-6 in good overall yields and high enantiomeric excesses of up to 97%.

  DOI：

  10.1016/s0040-4020(01)87015-0
• 作为产物：
  描述：

  (S)-1-amino-2-(methoxymethyl)pyrrolidine 、 乙醛 以89%的产率得到(S)-(-)-1-(ethylideneamino)-2-(methoxymethyl)pyrrolidine
  参考文献：
  名称：

  Enders, Dieter; Rendenbach, Beatrice E. M., Chemische Berichte, 1987, vol. 120, p. 1223 - 1228

  摘要：

  DOI：

文献信息

• Enantioselective synthesis of α-phosphanyl ketones and 2-phosphanyl alcohols
  作者：Dieter Enders、Thorsten Berg、Gerhard Raabe、Jan Runsink

  DOI：10.1002/jlac.199719970212

  日期：1997.2

  efficient, highly enantioselective methodology for the synthesis of α-phosphanyl ketones 7 and 2-phosphanyl alcohols 12 and 13, important hemilable ligands for enantioselective homogeneous catalysis and chiral building blocks in general, has been developed. The key step of this first enantio-selective synthesis of α-phosphanyl ketones is the diastereo-selective phosphanylation of SAMP hydrazones 2 to produce

  已经开发了一种有效的，高对映选择性的方法，用于合成α-膦酰基酮7和2-膦烷基醇12和13，这是对映选择性均相催化的重要重要半可配体，通常是手性结构单元。该α-膦酰基酮的第一对映选择性合成的关键步骤是SAMP hydr 2的非对映选择性膦酰基化反应，生成α-膦酰基an，被分离为更稳定的硼烷加合物6。随后的臭氧分解得到α-膦酰基酮7。2-膦烷基醇12和13的对映选择性合成已经通过两种根本不同的方法完成了该反应：未取代的手性醛9的膦酰基化和α-二苯基phoshanshan乙醛SAMP 10 10的烷基化。分离出次要的非对映异构体后，通过臭氧分解，还原和去除硼烷基团，将硼烷保护的α-膦酰基醛11转化为未保护的2-膦醇13。通过X射线分析，NOE实验或极化测定法确定官能化膦的绝对构型。
• Quinazoline Derivatives Having Tyrosine Kinase Inhibitory Activity
  申请人：Kume Masaharu

  公开号：US20090143414A1

  公开（公告）日：2009-06-04

  A compound which inhibits both of EGF receptor tyrosine kinase and HER2 tyrosine kinase is provided. A compound represented by the general formula (I): wherein R X is a group represented by the formula: wherein R 1 is a hydrogen atom, optionally substituted alkyl, etc.; Z is —O—, —N(R 10 )—, etc.; R 10 is a hydrogen atom, alkyl, etc.; R 2 is a hydrogen atom, optionally substituted alkyl, etc.; R 18 is a hydrogen atom, optionally substituted alkyl, etc.; R 19 is optionally substituted alkyl, etc.; W 1 is an optionally substituted non-aromatic nitrogen-containing group; R 17 is a hydrogen atom, optionally substituted alkyl, etc.; R 3 and R 4 are independently a hydrogen atom, optionally substituted alkyl, etc.; X is —O—, —S—, or —N(R 12 )—, etc.; R 12 is a hydrogen atom, alkyl, etc.; and A is phenyl optionally having a substituent, etc., its pharmaceutically acceptable salt, or a solvate thereof.

  提供了一种抑制EGF受体酪氨酸激酶和HER2酪氨酸激酶的化合物。该化合物由通式（I）表示：其中RX是由以下式子表示的基团：其中R1是氢原子，可选取代烷基等；Z是—O—，—N（R10）—等；R10是氢原子，烷基等；R2是氢原子，可选取代烷基等；R18是氢原子，可选取代烷基等；R19是可选取代烷基等；W1是可选取代非芳香族含氮基团；R17是氢原子，可选取代烷基等；R3和R4分别是氢原子，可选取代烷基等；X是—O—，—S—或—N（R12）—等；R12是氢原子，烷基等；A是苯基，可选取代基等，其药物可接受的盐或其溶剂化合物。
• QUINAZOLINE DERIVATIVES HAVING TYROSINE KINASE INHIBITORY ACTIVITY
  申请人：KUME Masaharu

  公开号：US20120123114A1

  公开（公告）日：2012-05-17

  A compound which inhibits both of EGF receptor tyrosine kinase and HER2 tyrosine kinase is provided. A compound represented by the general formula (I): wherein R X is a group represented by the formula: wherein R 1 is a hydrogen atom, optionally substituted alkyl, etc.; Z is —O—, —N(R 10 )—, etc.; R 10 is a hydrogen atom, alkyl, etc.; R 2 is a hydrogen atom, optionally substituted alkyl, etc.; R 18 is a hydrogen atom, optionally substituted alkyl, etc.; R 19 is optionally substituted alkyl, etc.; W 1 is an optionally substituted non-aromatic nitrogen-containing group; R 17 is a hydrogen atom, optionally substituted alkyl, etc.; R 3 and R 4 are independently a hydrogen atom, optionally substituted alkyl, etc.; X is —O—, —S—, or —N(R 12 )—, etc.; R 12 is a hydrogen atom, alkyl, etc.; and A is phenyl optionally having a substituent, etc., its pharmaceutically acceptable salt, or a solvate thereof.

  提供了一种同时抑制EGF受体酪氨酸激酶和HER2酪氨酸激酶的化合物。该化合物的普遍式表示为（I）：其中，RX是由以下式表示的基团：其中，R1是氢原子，可选地取代的烷基等；Z为—O—，—N(R10)—等；R10为氢原子，烷基等；R2为氢原子，可选地取代的烷基等；R18为氢原子，可选地取代的烷基等；R19为可选地取代的烷基等；W1为可选地取代的非芳香族含氮基团；R17为氢原子，可选地取代的烷基等；R3和R4分别为氢原子，可选地取代的烷基等；X为—O—，—S—或—N(R12)—等；R12为氢原子，烷基等；A为苯基，可选地具有取代基等，其药学上可接受的盐或其溶剂化物。
• ENDERS D.; RENDENBACH B. E. M., CHEM. BER., 120,(1987) N 7, 1223-1227
  作者：ENDERS D.、 RENDENBACH B. E. M.

  DOI：——

  日期：——
• US8202879B2
  申请人：——

  公开号：US8202879B2

  公开（公告）日：2012-06-19