3-(苄基氨基)-2-甲基-1-丙醇 | 858834-71-6

• 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: 3-(苄基氨基)-2-甲基-1-丙醇
• 中文别名: 3-(苄氨基)-2-甲基-丙-1-醇
• 英文名称: 3-(benzylamino)-2-methylpropan-1-ol
• CAS: 858834-71-6
• 化学式: C₁₁H₁₇NO
• 分子量: 179.262
• InChiKey: HJARAYMXDYVLBL-UHFFFAOYSA-N

物化性质

• 沸点：
  126 °C(Press: 1.0 Torr)
• 密度：
  1.004±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  13
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  32.3
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2922199090

反应信息

• 作为反应物：
  描述：

  3-(苄基氨基)-2-甲基-1-丙醇 在 四氧化锇 、 氯化亚砜 、 甲基磺酰胺 、 三氟化硼乙醚 、 Pseudomonas capacia enzyme 、 水 、 potassium carbonate 、 三乙胺 、 sodium hydroxide 、 lithium hydroxide 、 potassium hexacyanoferrate(III) 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙酸乙酯 、 甲苯 、 叔丁醇 为溶剂， 反应 65.67h， 生成 (2S,3S,4S)-N-benzyl-3-hydroxy-4-methylproline
  参考文献：
  名称：

  Stereoselective synthesis of N-benzyl (2S,3S,4S)-3-hydroxy-4-methylproline

  摘要：

  The synthesis of (2S,3S,4S)-N-benzyl-3-hydroxy 4-methyl proline and its stereoisomer (2R,3R,4S)-N-benzyl-3-hydroxy 4-methyl proline has been achieved starting with the conjugate addition of methyl methacrolate and benzylamine. The other key reactions performed in our strategy include enzymatic separation of an alpha-methyl beta-amino alcohol, Sharpless asymmetric dihydroxylation of an alpha,beta-unsaturated delta-amino ester, and intramolecular cyclization of a sulfonate to a pyrrolidine ring system. Two stereoisomers were synthesized from the common alpha,beta-unsaturated delta-amino ester intermediate. This protocol is simple, straightforward, efficient, highly stereoselective, and economically viable. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.008
• 作为产物：
  描述：

  3-苄氨基-2-甲基丙酸乙酯 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 3-(苄基氨基)-2-甲基-1-丙醇
  参考文献：
  名称：

  Stereoselective synthesis of N-benzyl (2S,3S,4S)-3-hydroxy-4-methylproline

  摘要：

  The synthesis of (2S,3S,4S)-N-benzyl-3-hydroxy 4-methyl proline and its stereoisomer (2R,3R,4S)-N-benzyl-3-hydroxy 4-methyl proline has been achieved starting with the conjugate addition of methyl methacrolate and benzylamine. The other key reactions performed in our strategy include enzymatic separation of an alpha-methyl beta-amino alcohol, Sharpless asymmetric dihydroxylation of an alpha,beta-unsaturated delta-amino ester, and intramolecular cyclization of a sulfonate to a pyrrolidine ring system. Two stereoisomers were synthesized from the common alpha,beta-unsaturated delta-amino ester intermediate. This protocol is simple, straightforward, efficient, highly stereoselective, and economically viable. (C) 2016 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2016.02.008

文献信息

• Novel transformation of α,β-unsaturated aldehydes and ketones into γ-amino alcohols or 1,3-oxazines via a 4 or 5 step, one-pot sequence
  作者：Adam D. J. Calow、Andrei S. Batsanov、Elena Fernández、Cristina Solé、Andrew Whiting

  DOI：10.1039/c2cc36129a

  日期：——

  An efficient, 4-step, one-pot, highly stereoselective route to γ-amino alcohols has been developed via an in situ α,β-unsaturated imine formation, β-boration, reduction (CN) and oxidation (C–B) sequence and especially for certain water-soluble γ-amino alcohols, a further step can be added to directly access the corresponding 1,3-oxazine derivatives.

  开发了一种高效的四步一锅法高度立体选择性合成γ-氨基醇的路线，通过原位形成α，β-不饱和亚胺、β-硼化、还原（CN）和氧化（C-B）的顺序，特别是对于某些水溶性γ-氨基醇，还可以增加一步直接获得相应的1,3-噁嗪衍生物。
• Heterocyclic compounds, their production and use
  申请人：——

  公开号：US20020132817A1

  公开（公告）日：2002-09-19

  A compound represented by the formula: 1 wherein ring M is a heterocyclic ring wherein —X═Y< is one of —N═C<, —CO—N< or —CS—N<; R a and R b are bonded to each other to form Ring A, or they are the same or different and represent, independently, a hydrogen atom or a substituent on the Ring M; Ring A and Ring B represent, independently, an optionally substituted homocyclic or heterocyclic ring, with the proviso that at least one of them is an optionally substituted heterocyclic ring; Ring C is an optionally substituted homocyclic or heterocyclic ring; Ring Z is an optionally substituted nitrogen-containing heterocyclic ring; and n is an integer from 1 to 6, or a salt thereof has a tachykinin receptor antagonistic activity in vitro, and is useful for preventing or treating depression, anxiety, manic-depressive illness or psychopathy.

  一种由以下通式表示的化合物：1，其中环M为杂环环，其中—X═Y<为—N═C<、—CO—N<或—CS—N<之一；Ra和Rb彼此连接形成环A，或者它们相同或不同，独立地表示氢原子或环M上的取代基；环A和环B独立地表示可任选取代的碳环或杂环环，条件是至少一个为可任选取代的杂环环；环C为可任选取代的碳环或杂环环；环Z为可任选取代的含氮杂环环；n为1至6的整数，或其盐在体外具有速激肽受体拮抗活性，并可用于预防或治疗抑郁症、焦虑症、双相情感障碍或精神病。
• TYK2 INHIBITORS AND USES THEREOF
  申请人：Nimbus Lakshmi, Inc.

  公开号：US20190031664A1

  公开（公告）日：2019-01-31

  The present invention provides compounds, compositions thereof, and methods of using the same for the inhibition of TYK2, and the treatment of TYK2-mediated disorders.

  本发明提供了化合物、其组合物以及使用这些化合物来抑制TYK2以及治疗TYK2介导的疾病的方法。
• Formal Nitrene Insertion into the β-Vinyl C–H Bond of Acroleins: Synthesis of Enaminals
  作者：Dongsheng Zhang、Huatao Zheng、Lei Zeng、Yi Nie、Yingzhu Fan、Weidong Rao、Lizhu Gao

  DOI：10.1021/acs.orglett.2c04028

  日期：2023.1.13

  nitrene insertion reaction into the β-vinyl C–H bond of acroleins with an electron-rich organic azide was developed. The reaction protocol can produce secondary enaminals in high yield with a broad substrate scope. In the reaction, acid mediated [3 + 2] cycloaddition of organic azides with an acrolein generated intermediate protonated triazolines, which were selectively decomposed into enaminals with

  开发了一种有效的形式氮烯插入丙烯醛的 β-乙烯基 C-H 键与富电子有机叠氮化物的反应。该反应方案可以产生具有广泛底物范围的高产率次级烯胺。在反应中，酸介导的有机叠氮化物与丙烯醛的 [3 + 2] 环加成生成中间体质子化三唑啉，通过加入弱布朗斯台德碱性试剂（例如甲醇）将其选择性地分解成烯胺醛。在温和的氢化条件下，生成的仲烯醛很容易还原成 γ-氨基醇。
• DRUGS
  申请人：Takeda Chemical Industries, Ltd.

  公开号：EP1145714A1

  公开（公告）日：2001-10-17

  The present invention relates to a medicine which comprises a compound (I) of the formula: [wherein the ring M is a heterocylic ring having -N=C<, -CO-N< or -CS-N< as a partial structure ―X=Y〈, Ra and Rb are bound to each other to form the ring A, or they are the same or different each representing a hydrogen atom or a substituent on the ring M; the rings A and B each is an optionally substituted homocycle or heterocycle, and at least one of them is an optionally substituted heterocycle; the ring C is an optionally substituted homocycle or heterocycle; the ring Z is an optionally substituted nitrogen-containing heterocycle; and n is an integer of 1 to 6] or a salt thereof in combination with a drug having an emetic action. The compounds (I) or their salts are useful as anti-emetic drugs. Particularly, vomiting caused by drugs having an emetic action can be inhibited by these compounds rapidly and safely at a low dose.

  本发明涉及一种药物，该药物由式(I)化合物组成： [其中环 M 是杂环，具有-N＝C〈、-CO-N〈或-CS-N〈作为部分结构-X＝Y〈、 Ra 和 Rb 相互结合形成环 A，或者它们相同或不同，各自代表环 M 上的一个氢原子或一个取代基； 环 A 和环 B 各自是任选取代的均环或杂环，其中至少一个是任选取代的杂环； 环 C 是任选取代的均环或杂环 环 Z 是任选取代的含氮杂环；以及 n 是 1 至 6 的整数］ 或其盐与具有催吐作用的药物结合使用。 化合物 (I) 或其盐类可用作止吐药。特别是，具有催吐作用的药物引起的呕吐，可以通过这些化合物以低剂量快速安全地抑制。