(R)-1-phenyl-2-propinylamine | 226699-01-0

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-1-phenyl-2-propinylamine
• 英文别名: (S)-1-phenyl-2-propynylamine；(S)-1-phenylprop-2-yn-1-amine；(1S)-1-phenylprop-2-yn-1-amine
• CAS: 226699-01-0
• 化学式: C₉H₉N
• 分子量: 131.177
• InChiKey: WTZFFHKYDKHUSG-VIFPVBQESA-N

物化性质

• 沸点：
  209.8±20.0 °C(Predicted)
• 密度：
  1.033±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  10
• 可旋转键数：
  1
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  26
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3S,6S,10AS)-6-((叔丁氧基羰基)氨基)-5-氧杂十二烷基氢吡咯并[1,2-A]偶氮辛-3-羧酸 、 (R)-1-phenyl-2-propinylamine 在 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 8.0h， 生成
  参考文献：
  名称：

  Design, Synthesis, and Characterization of a Potent, Nonpeptide, Cell-Permeable, Bivalent Smac Mimetic That Concurrently Targets Both the BIR2 and BIR3 Domains in XIAP

  摘要：

  XIAP is a central apoptosis regulator that inhibits apoptosis by binding to and inhibiting the effectors caspase-3/-7 and an initiator caspase-9 through its BIR2 and BIR3 domains, respectively. Smac protein in its dimeric form effectively antagonizes XIAP by concurrently, targeting both its BIR2 and BIR3 domains. We report the design, synthesis, and characterization of a nonpeptide, cell-permeable, bivalent small-molecule (SM-164) which mimics Smac protein for targeting XIAP. Our study shows that SM-164 binds to XIAP containing both BIR domains with an IC50 value of 1.39 nM, being 300 and 7000 times more potent than its monovalent counterparts and the natural Smac AVPI peptide, respectively. SM-164 concurrently interacts with both BIR domains in XIAP and functions as an ultrapotent antagonist of XIAP in both cell-free functional and cell-based assays. SM-164 targets cellular XIAP and effectively induces apoptosis at concentrations as low as 1 nM in the HL-60 leukemia cell line. The potency of bivalent SM-164 in binding, functional, and cellular assays is 2-3 orders of magnitude higher than its corresponding monovalent Smac mimetics.

  DOI：

  10.1021/ja074725f
• 作为产物：
  描述：

  (+/-)-1-苯基-2-丙炔-1-醇 在 CAL-B 盐酸 、 硫酸 作用下， 以 乙醚 为溶剂， 生成 (R)-1-phenyl-2-propinylamine
  参考文献：
  名称：

  微波辅助点击化学合成对映体纯的α-[4-（1-取代）-1,2,3-三唑-4-基]-苄基乙酰胺：寻求新的潜在抗微生物剂

  摘要：

  手性1-苯基-2-丙炔基胺是合成与联苯苄唑有关的抗真菌剂和抗芳香酶的重要组成部分。在此报告中，已采用微波辅助的Cu（I）催化的“点击化学”方法轻松生成对映体纯的α-[4-（1-取代）-1,2,3-三唑-从外消旋炔丙基胺开始的4-基]苄基乙酰胺。这些化合物可以代表用于合成新的抗微生物剂的容易获得的中间体。

  DOI：

  10.1016/j.tetasy.2007.06.007

文献信息

• Gold and Biocatalysis for the Stereodivergent Synthesis of Nor(pseudo)ephedrine Derivatives: Cascade Design Toward Amino Alcohols, Diols, and Diamines
  作者：Sergio González‐Granda、Georg Steinkellner、Karl Gruber、Iván Lavandera、Vicente Gotor‐Fernández

  DOI：10.1002/adsc.202300140

  日期：——

  derivatives in a regio- and stereoselective manner. The approach involves developing IPrAuNTf2-catalyzed hydration of 1-phenylprop-2-yn-1-yl acetate or N-(1-phenylprop-2-yn-1-yl)acetamide, followed by (dynamic) asymmetric biotransamination or bioreduction of the corresponding keto ester or keto amide intermediates. Enzyme actions were completely selective towards the modification of the methyl ketones in a highly

  金 (I) 和酶催化的结合以区域选择性和立体选择性的方式提供了一系列去甲（伪）麻黄碱衍生物的途径。该方法涉及开发 IPrAuNTf 2 -催化水合的 1-phenylprop-2-yn-1-yl 乙酸盐或N-(1-phenylprop-2-yn-1-yl)acetamide，然后是相应的酮酯或酮酰胺中间体的（动态）不对称生物转氨作用或生物还原。酶的作用对以高度立体选择性的方式修饰甲基酮具有完全选择性，允许使用外消旋或光学活性起始材料合成对映体和非对映体富集的产物。因此，一系列氨基醇、二醇和二胺衍生物由炔丙酯或酰胺（57% 至 86% 的分离产率）产生，选择的生物催化剂决定了整个级联过程的（立体）选择性（70-99% 非对映体过量和 >98% 对映体过量），并以直接的方式提供对去甲（伪）麻黄碱化合物的访问。
• Resolution of (±)-1-Aryl-2-propynylamines via Acyltransfer Catalyzed by <i>Candida antarctica</i> Lipase
  作者：Flavia Messina、Maurizio Botta、Federico Corelli、Manfred P. Schneider、Fabio Fazio

  DOI：10.1021/jo982513i

  日期：1999.5.1
• Microwave-assisted ethylene–alkyne cross-metathesis: synthesis of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes
  作者：Daniele Castagnolo、Michela L. Renzulli、Elena Galletti、Federico Corelli、Maurizio Botta

  DOI：10.1016/j.tetasy.2005.08.002

  日期：2005.9

  Chiral 1-arylpropargyl amides, which are resistant to undergoing ethylene-alkyne cross-metathesis at atmospheric pressure, were reacted under microwave irradiation to afford enantiomerically enriched 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes within a few minutes. Enantiomerically enriched amides underwent ethylene-alkyne cross-metathesis with retention of configuration at the propargylic/allylic position. A series of chiral 2-(N-1-acetyl-1-arylmethyl)-1,3-butadienes were synthesised with ee >= 95%; these latter compounds could be used as building blocks for the synthesis of new antifungal and antiaromatase agents. (c) 2005 Elsevier Ltd. All rights reserved.
• Stereoselective synthesis of α-aryl-2-benzofuranmethanamines and α-aryl-1H-indole-2-methanamines through palladium-mediated annulation of chiral α-arylpropargylamines
  作者：Flavia Messina、Maurizio Botta、Federico Corelli、Claudio Villani

  DOI：10.1016/s0957-4166(00)00131-2

  日期：2000.5

  The title compounds, valuable chiral synthons for the synthesis of biologically active compounds, have been prepared in good yield and with high stereoselectivity through palladium-catalyzed heteroannulation of 2-iodophenol or 2-iodo-N-mesylaniline with enantiomerically pure or enriched alpha-arylpropargylamines. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Chiral Azole Derivatives. 4.¹ Enantiomers of Bifonazole and Related Antifungal Agents:  Synthesis, Configuration Assignment, and Biological Evaluation
  作者：Maurizio Botta、Federico Corelli、Francesco Gasparrini、Flavia Messina、Claudia Mugnaini

  DOI：10.1021/jo991937p

  日期：2000.7.1