(2R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(3,4-dichlorophenyl)butane-1,2-diol | 191673-32-2

• 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: (2R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(3,4-dichlorophenyl)butane-1,2-diol
• CAS: 191673-32-2
• 化学式: C₁₆H₂₆Cl₂O₃Si
• 分子量: 365.372
• InChiKey: HIOQXYWZDIYGST-INIZCTEOSA-N

物化性质

• 沸点：
  438.7±45.0 °C(Predicted)
• 密度：
  1.155±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.59
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(3,4-dichlorophenyl)butane-1,2-diol 在 吡啶 、 盐酸 、 lithium perchlorate 、 三乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 甲苯 、 乙腈 为溶剂， 生成 (2R)-2-[2-(3,4-dichlorophenyl)-4-(3,4,5-trimethoxybenzoyl)morpholin-2-yl]ethanol
  参考文献：
  名称：

  速激肽受体拮抗剂联合：新型吗啉类似物的合成与立体化学结构-活性关系。

  摘要：

  我们在此报告了关于NK1，NK2和NK3速激肽受体结合亲和力的新型吗啉类似物12和13的合成和立体化学结构-活性关系。绝对构型控制了对更有效的结合亲和力的基本要求。（S，R）-12和（S，R）-13对NK1，NK2和NK3受体表现出高结合亲和力。

  DOI：

  10.1016/s0960-894x(00)00324-3
• 作为产物：
  描述：

  3,4-二氯溴苯 在 bis-triphenylphosphine-palladium(II) chloride 、 AD-mix-β 、 碘 、 magnesium 作用下， 以 水 、 叔丁醇 为溶剂， 反应 11.25h， 生成 (2R)-4-[tert-butyl(dimethyl)silyl]oxy-2-(3,4-dichlorophenyl)butane-1,2-diol
  参考文献：
  名称：

  An efficient synthesis of enantiomerically pure 2-[(2R)-arylmorpholin-2-yl]ethanols, key intermediates of tachykinin receptor antagonist

  摘要：

  We report herein an efficient and practical synthetic method for the preparation of enantiomerically pure 2[(2R)-arylmorpholin-2-yl]ethanols 1a-d, key intermediates of tachykinin receptor antagonist. Sharpless catalytic asymmetric dihydroxylation of 4a-d was employed to introduce the required absolute stereochemistry, and cyclization of 7a-d was accomplished by the Mitsunobu reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00336-x

文献信息

• Combined NK1 and NK2 tachykinin receptor antagonists: Synthesis and structure-activity relationships of novel oxazolidine analogues
  作者：Takahide Nishi、Tetsuya Fukazawa、Koki Ishibashi、Katsuyoshi Nakajima、Yuki Sugioka、Yukiko Iio、Hitoshi Kurata、Kazuhiro Itoh、Osamu Mukaiyama、Yumiko Satoh、Takeshi Yamaguchi

  DOI：10.1016/s0960-894x(99)00093-1

  日期：1999.3

  We report herein the synthesis and structure-activity relationships of a series of novel oxazolidine analogues with regards to NK1 and NK2 tachykinin receptor binding affinity. Among this series of oxazolidine analogues, some compounds exhibited excellent high binding affinities for both NK1 and NK2 receptors. In addition, we describe the inhibitory effect in vivo on SP-induced airway vascular hyperpermeability and NKA-induced bronchoconstriction in guinea pigs. (C) 1999 Elsevier Science Ltd. All rights reserved.
• An efficient synthesis of enantiomerically pure 2-[(2R)-arylmorpholin-2-yl]ethanols, key intermediates of tachykinin receptor antagonist
  作者：Takahide Nishi、Koki Ishibashi、Katsuyoshi Nakajima、Yukiko Iio、Tetsuya Fukazawa

  DOI：10.1016/s0957-4166(98)00336-x

  日期：1998.9

  We report herein an efficient and practical synthetic method for the preparation of enantiomerically pure 2[(2R)-arylmorpholin-2-yl]ethanols 1a-d, key intermediates of tachykinin receptor antagonist. Sharpless catalytic asymmetric dihydroxylation of 4a-d was employed to introduce the required absolute stereochemistry, and cyclization of 7a-d was accomplished by the Mitsunobu reaction. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Combined tachykinin receptor antagonist: synthesis and stereochemical structure–activity relationships of novel morpholine analogues
  作者：Takahide Nishi、Koki Ishibashi、Toshiyasu Takemoto、Katsuyoshi Nakajima、Tetsuya Fukazawa、Yukiko Iio、Kazuhiro Itoh、Osamu Mukaiyama、Takeshi Yamaguchi

  DOI：10.1016/s0960-894x(00)00324-3

  日期：2000.8

  We report herein the synthesis and stereochemical structure-activity relationships of novel morpholine analogues 12 and 13 with regards to NK1, NK2 and NK3 tachykinin receptor binding affinity. An essential requirement for more potent binding affinities was controlled by absolute configuration. (S,R)-12 and (S,R)-13 exhibited high binding affinities for NK1, NK2 and NK3 receptors.

  我们在此报告了关于NK1，NK2和NK3速激肽受体结合亲和力的新型吗啉类似物12和13的合成和立体化学结构-活性关系。绝对构型控制了对更有效的结合亲和力的基本要求。（S，R）-12和（S，R）-13对NK1，NK2和NK3受体表现出高结合亲和力。