(S)-(-)-2-benzyloxycyclobutanone | 737758-92-8

• 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: (S)-(-)-2-benzyloxycyclobutanone
• 英文别名: (S)-2-(Benzyloxy)cyclobutanone；(2S)-2-phenylmethoxycyclobutan-1-one
• CAS: 737758-92-8
• 化学式: C₁₁H₁₂O₂
• 分子量: 176.215
• InChiKey: HRPGUVFWKDCSSX-NSHDSACASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (S)-(-)- α-甲基苄胺 、 氰化钠 、 (S)-(-)-2-benzyloxycyclobutanone 在 溶剂黄146 作用下， 以 二甲基亚砜 为溶剂， 反应 5.0h， 以40%的产率得到(1S,2S,1'S)-2-benzyloxy-1-[(1'-phenylethyl)amino]cyclobutanecarbonitrile
  参考文献：
  名称：

  由外消旋或旋光的2-苄氧基环丁酮立体选择性合成（1 R，2 R）-1-氨基-2-羟基环丁烷羧酸-丝氨酸衍生物

  摘要：

  通过不对称的Strecker合成，由容易获得的2-苄氧基环丁酮进行的简单高效的一锅反应可生成具有良好选择性的动力学或热力学腈。分离后，将主要的反式-氨基腈进行碱性水解和氢解，然后进行酸性水解，得到旋光性的（1 R，2 R）-1-氨基-2-羟基环丁烷羧酸，丝氨酸衍生物。通过对相应的顺式-氨基腈的X射线分析已经确定了绝对构型。

  DOI：

  10.1016/j.tetasy.2006.05.014
• 作为产物：
  描述：

  (S)-(+)-2-benzyloxycyclobutanone dimethyl acetal 在 硫酸 、 silica gel 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以91%的产率得到(S)-(-)-2-benzyloxycyclobutanone
  参考文献：
  名称：

  The first synthesis of both enantiomers of 2-hydroxycyclobutanone acetals by enzymatic transesterification: preparation of (R)-(+)-2-benzyloxycyclobutanone and its antipode

  摘要：

  A new practical enzymatic synthesis of (R)-(+)- and (S)-(-)-2-acetoxycyclobutanone acetals with 97-99.9% ee has been carried out via enzymatic transesterification of readily available racemic 2-hydroxycyclobutanone acetals. The absolute configuration has been established by X-ray analysis of the corresponding (S)-naproxenyl derivative. The first preparation of enantiomerically pure (R)-(+)- and (S)- (-)-2- benzyloxycyclobutanones was accomplished by means of protection of the hydroxy group followed by deacetalation reaction. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.04.016

文献信息

• PYRROLOTRIAZINE DERIVATIVES FOR TREATING KIT-AND PDGFRA-MEDIATED DISEASES
  申请人：Blueprint Medicines Corporation

  公开号：US20220153748A1

  公开（公告）日：2022-05-19

  The present disclosure provides compounds of Formula I, pharmaceutical salts thereof, and/or solvates of any of the foregoing which are useful for treating diseases and conditions related to mutant KIT and PDGFRa and present an advantageously non-brain penetrant profile for treating diseases and conditions related to mutant KIT and PDGFRa. The present disclosure also provides methods for treating gastrointestinal stromal tumors and systemic mastocytosis.
• [EN] 1-PYRAZOLYL, 5-, 6- DISUBSTITUTED INDAZOLE DERIVATIVES AS LRRK2 INHIBITORS, PHARMACEUTICAL COMPOSITIONS, AND USES THEREOF<br/>[FR] DÉRIVÉS D'INDAZOLE 5 -, 6-DISUBSTITUÉS, 1-PYRAZOLYLE, EN TANT QU'INHIBITEURS DE LRRK2, COMPOSITIONS PHARMACEUTIQUES ET UTILISATIONS CORRESPONDANTES
  申请人：MERCK SHARP & DOHME

  公开号：WO2020247298A2

  公开（公告）日：2020-12-10

  The present invention is directed to substituted certain 1-pyrazolyl, 5-, 6- disubstituted indazole derivatives of Formula (I) and pharmaceutically acceptable salts thereof, wherein R1, R2, and ring A are as defined herein, which are potent inhibitors of LRRK2 kinase and may be useful in the treatment or prevention of diseases in which the LRRK2 kinase is involved, such as Parkinson's Disease and other diseases and disorders described herein. The invention is also directed to pharmaceutical compositions comprising these compounds and the use of these compounds and compositions in the prevention or treatment of diseases, such as Parkinson's disease, in which LRRK-2 kinase is involved.
• Stereoselective synthesis of (1R,2R)-1-amino-2-hydroxycyclobutanecarboxylic acid—serine derivative—, from racemic or optically active 2-benzyloxycyclobutanone
  作者：Damien Hazelard、Antoine Fadel、Christian Girard

  DOI：10.1016/j.tetasy.2006.05.014

  日期：2006.5

  one-pot reaction from readily available 2-benzyloxycyclobutanone gave, by means of an asymmetric Strecker synthesis, a kinetic or thermodynamic nitrile with good selectivity. After separation, the major trans-amino nitrile underwent basic hydrolysis and hydrogenolysis, followed by acidic hydrolysis, to give optically active (1R,2R)-1-amino-2-hydroxycyclobutanecarboxylic acid, serine derivative. The absolute

  通过不对称的Strecker合成，由容易获得的2-苄氧基环丁酮进行的简单高效的一锅反应可生成具有良好选择性的动力学或热力学腈。分离后，将主要的反式-氨基腈进行碱性水解和氢解，然后进行酸性水解，得到旋光性的（1 R，2 R）-1-氨基-2-羟基环丁烷羧酸，丝氨酸衍生物。通过对相应的顺式-氨基腈的X射线分析已经确定了绝对构型。
• The first synthesis of both enantiomers of 2-hydroxycyclobutanone acetals by enzymatic transesterification: preparation of (R)-(+)-2-benzyloxycyclobutanone and its antipode
  作者：Damien Hazelard、Antoine Fadel、Georges Morgant

  DOI：10.1016/j.tetasy.2004.04.016

  日期：2004.6

  A new practical enzymatic synthesis of (R)-(+)- and (S)-(-)-2-acetoxycyclobutanone acetals with 97-99.9% ee has been carried out via enzymatic transesterification of readily available racemic 2-hydroxycyclobutanone acetals. The absolute configuration has been established by X-ray analysis of the corresponding (S)-naproxenyl derivative. The first preparation of enantiomerically pure (R)-(+)- and (S)- (-)-2- benzyloxycyclobutanones was accomplished by means of protection of the hydroxy group followed by deacetalation reaction. (C) 2004 Elsevier Ltd. All rights reserved.