(R)-CBS

• 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: (R)-CBS
• 英文别名: (3aR)-3,3-diphenyl-3a,4,5,6-tetrahydro-1H-pyrrolo[1,2-c][1,3,2]oxazaborole
• 化学式: C₁₇H₁₈BNO
• 分子量: 263.147
• InChiKey: NSAZIMJIRLGSEG-MRXNPFEDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.69
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  12.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-甲基环戊烯 、 (R)-CBS 在 bis(cyclohexanyl)borane 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 4.0h， 生成 trans-(2-Methylcyclopentyl)boronate
  参考文献：
  名称：

  反式-2-取代环烷基三氟硼酸钾的合成方法

  摘要：

  本发明公开了反式‑2‑取代环己基三氟硼酸钾的合成方法，属于有机合成领域。从环酮出发与格氏试剂或锂试剂加成随后脱水得到取代烯烃，随后与邻苯二酚硼烷或脯胺醇硼烷加成反应后，氟氢化钾直接淬灭处理后得到反式‑2‑取代环己基三氟硼酸钾，采用邻苯二酚硼烷得到消旋体产品，手性脯胺醇硼烷得到对映纯产品。该方法成本低廉，原料来源方便，操作简单，具有工业化放大的前景。

  公开号：

  CN109503639B
• 作为产物：
  描述：

  (R)-(+)-alpha,alpha-二苯基脯氨醇 在 硼烷四氢呋喃络合物 作用下， 生成 (R)-CBS
  参考文献：
  名称：

  使用聚合物负载的 Corey-Bakshi-Shibata 催化剂高效合成 (R)-去氧肾上腺素

  摘要：

  报道了使用 Corey-Bakshi-Shibata (CBS) 催化剂制备 (R)-去氧肾上腺素盐酸盐的有效且温和的合成路线。为避免均相反应的催化剂回收过程冗长，制备了聚合物负载的CBS催化剂，并初步尝试在实验室规模上实现连续还原，有助于(R)-去氧肾上腺素的合成以具有成本效益的方式。

  DOI：

  10.1246/cl.170028
• 作为试剂：
  描述：

  (E)-1-(tert-butyldimethylsilyl)-3-phenylprop-2-en-1-one 在 (R)-CBS 、 dimethyl sulfide borane 作用下， 以 四氢呋喃 为溶剂， 反应 2.25h， 以79%的产率得到(E)-1-(tert-butyldimethylsilyl)-3-phenylprop-2-en-1-ol
  参考文献：
  名称：

  Stereoselective anti-SN2′ Mitsunobu reaction of α-hydroxy-α-alkenylsilanes

  摘要：

  A novel silyl group-directed anti-S(N)2' reaction of allylic alcohols under Mitsunobu reaction conditions is described. The Mitsunobu reaction of alpha-hydroxy-alpha-alkenylsilanes with a TBS or TIPS group gave the anti-S(N)2' product, in which regio- and stereochemical outcomes of the reaction depended on the steric bulkiness of the silyl group. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.080

文献信息

• Ethanolamine derivatives having sympathomimetic and anti-pollakiuria
  申请人：Fujisawa Pharmaceutical Co., Ltd.

  公开号：US05387710A1

  公开（公告）日：1995-02-07

  This invention relates to new ethanolamine derivatives having gut selective sympathomimetic and anti-pollakiuria activities and represented by the general formula [I]: ##STR1## wherein R.sup.1 is aryl or a heterocyclic group, each of which may be substituted with halogen, etc., R.sup.2 is hydrogen, halogen, nitro, hydroxy, lower alkyl optionally substituted with acyl, lower alkenyl optionally substituted with acyl, lower alkoxy optionally substituted with acyl, or amino optionally substituted with acyl(lower)alkyl, R.sup.3 is hydrogen, an N-protective group, or lower alkyl optionally substituted with lower alkylthio, n is an integer of 0 to 3, and a heavy solid line means a single bond or a double bond, provided that when n is 1, then 1) R.sup.1 is a condensed aromatic hydrocarbon group or a heterocyclic group, each of which may be substituted with halogen, etc., and the like, and pharmaceutically acceptable salts thereof to processes for the preparation thereof and to a pharmaceutical composition comprising the same.

  这项发明涉及具有肠道选择性交感兴奋作用和抗多尿活性的新乙醇胺衍生物，其通式为[I]：其中R.sup.1是芳基或杂环基，每个都可以用卤素等取代，R.sup.2是氢、卤素、硝基、羟基、可选择用酰基取代的较低烷基、可选择用酰基取代的较低烯基、可选择用酰基取代的较低烷氧基、或者可选择用酰基（较低）烷基取代的氨基，R.sup.3是氢、N-保护基，或者可选择用较低烷基硫代取代的较低烷基，n是0到3的整数，重实线表示单键或双键，但当n为1时，则1）R.sup.1是缩合芳香烃基或杂环基，每个都可以用卤素等取代，等等，以及其药学上可接受的盐，以及制备它们的方法和包含相同的药物组合。
• A Highly Effective Ruthenium System for the Catalyzed Dehydrogenative Cyclization of Amine-Boranes to Cyclic Boranes under Mild Conditions
  作者：Christopher J. Wallis、Gilles Alcaraz、Alban S. Petit、Amalia I. Poblador-Bahamonde、Eric Clot、Christian Bijani、Laure Vendier、Sylviane Sabo-Etienne

  DOI：10.1002/chem.201501569

  日期：2015.9.7

  disclosed a new ruthenium‐catalyzed dehydrogenative cyclization process (CDC) of diamine–monoboranes leading to cyclic diaminoboranes. In the present study, the CDC reaction has been successfully extended to a larger number of diamine–monoboranes (4–7) and to one amine–borane alcohol precursor (8). The corresponding NB(H)N‐ and NB(H)O‐containing cyclic diaminoboranes (12–15) and oxazaborolidine (16) were

  我们最近披露了一种新的钌催化的二胺-单硼烷烷的脱氢环化过程（CDC），可形成环状的二氨基硼烷。在本研究中，CDC反应已经成功地扩展到二胺- monoboranes（更大数目的4 - 7）和一种胺-硼烷醇前体（8）。相应的NB（H）N-和NB（H）O含环状diaminoboranes（12 - 15）和恶唑硼烷（16）以高到高的产量获得。评估了起始胺-硼烷底物上的多种取代方式，并且还使用手性底物进行了反应。已经花了很多努力来了解钌CDC流程的机制。除了计算方法外，还对六碳链二胺一硼烷21进行了能够对导致NB（H）N键形成的催化过程的连续事件进行动力学区分的策略，并用15 N NMR研究。具有反应性NHMe末端的长寿命双-σ-硼烷钌中间体23进行了原位表征，并被证明可催化1的脱氢环化，确定双σ-硼烷钌配合物是CDC过程中的关键中间体。
• Asymmetric synthesis of new chiral long chain alcohols
  作者：Tülay Yıldız、Ayşe Yusufoğlu

  DOI：10.1016/j.tetasy.2010.12.010

  日期：2010.12

  Sixteen new chiral alcohols with alkyl (C-11-C-19) and aryl, substituted aryl, hetero aryl and biaryl groups 2a-2t were synthesized by three different asymmetric reduction methods from their corresponding ketones 1a-1t. Chiral NaBH4 (method A), chiral BH3 (method B) and chiral AIP (method C) were used as asymmetric reduction catalysts. Chiral NaBH4 was modified by four different ligands 3a-3d, chiral BH3 and chiral AIP by four different ligands 4a-4d. Ligand 4c was synthesized for the first time in this work. Chiral NaBH4 generated chiral alcohols of (R)-configuration and chiral BH3 and chiral AIP of (S)-configuration with high enantiomeric excesses, were analysed by chiral HPLC. In order to determine the ee values by chiral HPLC, sixteen corresponding racemic alcohols, synthesized by reducing their corresponding ketones via NaBH4, were used for chiral resolution on a Daicel OD HPLC column. The sixteen starting ketones were synthesized in this study by Friedel-Craft acylation. The new chiral alcohols were characterized by IR, NMR, (H-1 and C-13), MS, elemental analyses and specific rotation. The reduction methods A, B and C were applied to these ketones for the first time in this study and were compared with each other. The relationship between the structure of the ketone and the yield and the enantiomeric excess was discussed. (C) 2010 Elsevier Ltd. All rights reserved.
• Is It Possible To Estimate the Enantioselectivity of a Chiral Catalyst from Its Racemic Mixture?
  作者：Franz Lagasse、Masaki Tsukamoto、Christopher J. Welch、Henri B. Kagan

  DOI：10.1021/ja0300315

  日期：2003.6.1

  The evaluation of a racemic catalyst was investigated in the case of oxazaborolidine (OAB)-catalyzed borane reduction of 1,5-diphenyl-1,5-pentanedione, giving the corresponding diol. On the basis of the diastereoselectivity of the diols, it is possible to estimate the enantioselectivity (ee) of the first step, which correlates well with the ee in the reaction of the structurally similar phenyl n-pentyl ketone with enantiopure OAB catalyst. The measure of diastereoselectivity could be a tool for screening racemic catalysts without the need for resolving the individual enantiomers, if in the second step of the process there is no substrate control and no catalyst scrambling.
• 反式-2-取代环烷基三氟硼酸钾的合成方法
  申请人：沧州普瑞东方科技有限公司

  公开号：CN109503639B

  公开（公告）日：2021-04-16

  本发明公开了反式‑2‑取代环己基三氟硼酸钾的合成方法，属于有机合成领域。从环酮出发与格氏试剂或锂试剂加成随后脱水得到取代烯烃，随后与邻苯二酚硼烷或脯胺醇硼烷加成反应后，氟氢化钾直接淬灭处理后得到反式‑2‑取代环己基三氟硼酸钾，采用邻苯二酚硼烷得到消旋体产品，手性脯胺醇硼烷得到对映纯产品。该方法成本低廉，原料来源方便，操作简单，具有工业化放大的前景。