(R,R)-tert-butyl 3-hydroxy-4-phenyl-piperidine-1-carboxylate | 357608-32-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: (R,R)-tert-butyl 3-hydroxy-4-phenyl-piperidine-1-carboxylate
• 英文别名: (+)-tert-butyl (3R,4R)-3-hydroxy-4-phenylpiperidine-1-carboxylate；rac-tert-butyl (3R,4R)-3-hydroxy-4-phenylpiperidine-1-carboxylate, trans；tert-butyl (3R,4R)-3-hydroxy-4-phenylpiperidine-1-carboxylate
• CAS: 357608-32-3
• 化学式: C₁₆H₂₃NO₃
• 分子量: 277.364
• InChiKey: HWNKSGVMOCONJS-KGLIPLIRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  49.8
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R,R)-tert-butyl 3-hydroxy-4-phenyl-piperidine-1-carboxylate 在 盐酸 作用下， 以 1,4-二氧六环 为溶剂， 生成 (3R,4R)-3-(4-Bromo-benzyloxy)-4-phenyl-piperidine; compound with trifluoro-acetic acid
  参考文献：
  名称：

  Solid-Phase Synthesis of Aspartic Peptidase Inhibitors:  3-Alkoxy-4-Aryl Piperidines

  摘要：

  [GRAPHICS]The 3-alkoxy-4-aryl piperidines are non-peptide peptidomimetic inhibitors of several aspartic peptidases. The solid-phase functionalization of 3,4-disubstituted piperidine scaffolds using a traceless linker strategy is described. Synthesis of diverse analogues based on this scaffold provides the potential to generate selective inhibitors of this important class of peptidase.

  DOI：

  10.1021/ol016280k
• 作为产物：
  描述：

  1,2,3,6-四氢-4-苯基吡啶盐酸盐 在 镍 4-二甲氨基吡啶 、 AD-mix-α 、 甲基磺酰胺 、 三乙胺 作用下， 以 乙醇 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 5.0h， 生成 (R,R)-tert-butyl 3-hydroxy-4-phenyl-piperidine-1-carboxylate
  参考文献：
  名称：

  从肽到非肽拟肽：天门冬氨酸肽酶新哌啶抑制剂的设计和合成。

  摘要：

  [反应：见正文]天冬氨酸肽酶的3-烷氧基-4-芳基哌啶抑制剂被证明是一种新型的非肽拟肽抑制剂。这些哌啶可通过使用结构生成程序由肽衍生的抑制剂设计，但仅在以机械相关方式修饰了酶活性位点构象之后。描述了3-烷氧基-4-芳基哌啶类似物的新的对映选择性合成。

  DOI：

  10.1021/ol016092u

文献信息

• Highly Enantioselective Organocatalytic Oxidative Kinetic Resolution of Secondary Alcohols Using Chiral Alkoxyamines as Precatalysts: Catalyst Structure, Active Species, and Substrate Scope
  作者：Keiichi Murakami、Yusuke Sasano、Masaki Tomizawa、Masatoshi Shibuya、Eunsang Kwon、Yoshiharu Iwabuchi

  DOI：10.1021/ja509766f

  日期：2014.12.17

  The development and characterization of enantioselective organocatalytic oxidative kinetic resolution (OKR) of racemic secondary alcohols using chiral alkoxyamines as precatalysts are described. A number of chiral alkoxyamines have been synthesized, and their structure-enantioselectivity correlation study in OKR has led us to identify a promising precatalyst, namely, 7-benzyl-3-n-butyl-4-oxa-5-azahomoadamantane

  描述了使用手性烷氧基胺作为预催化剂的外消旋仲醇的对映选择性有机催化氧化动力学拆分 (OKR) 的开发和表征。已经合成了许多手性烷氧基胺，它们在 OKR 中的结构-对映选择性相关性研究使我们确定了一种有前途的前催化剂，即 7-苄基-3-正丁基-4-氧杂-5-氮杂高金刚烷，它提供了各种手性脂肪族仲醇（ee 高达 >99%，k(rel) 高达 296）。在一项机理研究中，含氯氧铵物种被确定为烷氧基胺预催化剂原位生成的活性物种，并且发现氯原子对于高反应性和对映选择性至关重要。
• BICYCLIC HETEROCYCLIC DERIVATIVE
  申请人：Nakahira Hiroyuki

  公开号：US20110190278A1

  公开（公告）日：2011-08-04

  The present invention relates to a compound of the following formula (I) or a pharmaceutically acceptable salt thereof, being useful as a renin inhibitor. [wherein R 1a is halogen, etc.; R 1m is H, etc.; G 1 is —N(R 1b )—, etc.; G 2 is —CO—, etc.; G 3 is —C(R 1c )(R 1d )—, etc.; G 4 is oxygen, etc.; R 1b is optionally substituted C 1-6 alkyl, etc.; R 1c and R 1d are independently the same or different, H, etc.; R 3 is H, optionally substituted C 1-6 alkyl, etc.; R 3a , R 3b , R 3 c and R 3d are independently the same or different, and a group: -A-B (said A is single bond, etc., and said B is H, etc.), etc.; and n is 1, etc.]

  本发明涉及以下式（I）的化合物或其药学上可接受的盐，其可用作肾素抑制剂。[其中，R1a是卤素等；R1m是H等；G1是—N（R1b）—等；G2是—CO—等；G3是—C（R1c）（R1d）—等；G4是氧等；R1b是可选取代的C1-6烷基等；R1c和R1d独立选择为H等；R3是H、可选取代的C1-6烷基等；R3a、R3b、R3c和R3d独立选择为相同或不同的基团：-A-B（其中A是单键等，B是H等）等；n为1等。]
• From Peptides to Non-Peptide Peptidomimetics:  Design and Synthesis of New Piperidine Inhibitors of Aspartic Peptidases
  作者：Matthew G. Bursavich、Chris W. West、Daniel H. Rich

  DOI：10.1021/ol016092u

  日期：2001.7.1

  3-alkoxy-4-arylpiperidine inhibitors of aspartic peptidases are shown to be a new type of non-peptide peptidomimetic inhibitor. These piperidines can be designed from peptide-derived inhibitors by use of a structure-generating program but only after the enzyme active site conformation has been modified in a mechanistically related fashion. New enantioselective syntheses of 3-alkoxy-4-arylpiperidine analogues are

  [反应：见正文]天冬氨酸肽酶的3-烷氧基-4-芳基哌啶抑制剂被证明是一种新型的非肽拟肽抑制剂。这些哌啶可通过使用结构生成程序由肽衍生的抑制剂设计，但仅在以机械相关方式修饰了酶活性位点构象之后。描述了3-烷氧基-4-芳基哌啶类似物的新的对映选择性合成。
• Solid-Phase Synthesis of Aspartic Peptidase Inhibitors:  3-Alkoxy-4-Aryl Piperidines
  作者：Matthew G. Bursavich、Daniel H. Rich

  DOI：10.1021/ol016280k

  日期：2001.8.1

  [GRAPHICS]The 3-alkoxy-4-aryl piperidines are non-peptide peptidomimetic inhibitors of several aspartic peptidases. The solid-phase functionalization of 3,4-disubstituted piperidine scaffolds using a traceless linker strategy is described. Synthesis of diverse analogues based on this scaffold provides the potential to generate selective inhibitors of this important class of peptidase.