3,3-dimethyl-3-(N,N-dibenzyl)aminopropyne | 356519-33-0

• 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: 3,3-dimethyl-3-(N,N-dibenzyl)aminopropyne
• 英文别名: N,N-dibenzyl-1,1-dimethylpropargylamine；N,N-dibenzyl-2-methylbut-3-yn-2-amine
• CAS: 356519-33-0
• 化学式: C₁₉H₂₁N
• 分子量: 263.382
• InChiKey: NRVXHQVNGIHICY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  3.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3,3-dimethyl-3-(N,N-dibenzyl)aminopropyne 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  EP1179530

  摘要：

  公开号：
• 作为产物：
  描述：

  3-氯-3-甲基-1-丁炔 、 二苄胺 在 铜 、 三乙胺 、 copper(l) chloride 作用下， 以 乙醚 为溶剂， 生成 3,3-dimethyl-3-(N,N-dibenzyl)aminopropyne
  参考文献：
  名称：

  Aldehyde dehydrogenase inhibitors: α,β-Acetylenic N-substituted aminothiolesters are reversible growth inhibitors of normal epithelial but irreversible apoptogens for cancer epithelial cells from human prostate in culture

  摘要：

  The pharmacomodulation of the N atom of alpha,beta-acetylenic aminothiolesters or the replacement of the thiolester moiety by more electroplfflic groups did not permit any clear rationale to be established for improving the selective growth-inhibitory activity of this family of compounds over that of the previously synthesized alpha,beta-acetylenic aminothiolesters DIMATE and MATE [G. Quash, G. Fournet, J. Chantepie, J. Gore, C. Ardiet, D. Ardail, Y. Michal, U. Reichert, Biochem Phannacol 64 (2002) 1279-92]. Hence DIMATE and MATE were investigated more thoroughly for selectivity and growth-inhibitory activity using human prostate epithelial normal cells (HPENC) on the one hand and human prostate epithelial cancer cells (DU145) on the other. Unequivocal evidence was obtained showing that both compounds were reversible growth inhibitors of HPENC but irreversible growth inhibitors of DU145. Growth-inhibition of DU145 was due to the induction of early apoptosis as revealed by the flow cytometric analytical profile of inhibitor-treated cells, of the decrease in the redox potential and increase in superoxide anion content of their mitochondria. Of the two intracellular enzymes: aldehyde dehydrogenases 1 and 3 (ALDH1 and ALDH3) targeted by DIMATE and MATE, ALDH3 was inhibited to the same extent by both compounds whereas ALDH1 was less susceptible to inhibition by MATE. As the induction of ALDH3 by xenobiotics is hormone-dependent, MATE, the more selective of the two inhibitors, is a useful tool not only for examining the role of the ALDH3 isoform in hormone-sensitive and resistant prostate cancer cells in culture but also for investigating if it can inhibit the growth of xenografts of prostate cancer in immunodeficient mice. (C) 2007 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2007.06.004

文献信息

• Copper-Catalyzed Enantioselective Allylic Alkylation of Terminal Alkyne Pronucleophiles
  作者：Ayumi Harada、Yusuke Makida、Tatsunori Sato、Hirohisa Ohmiya、Masaya Sawamura

  DOI：10.1021/ja5084333

  日期：2014.10.1

  enantioselective allylic alkylation of terminal alkynes with primary allylic phosphates was developed by the use of a new chiral N-heterocyclic carbene ligand bearing a phenolic hydroxy group at the ortho position of one of the two N-aryl groups. This reaction occurred with excellent γ-branch regioselectivity and high enantioselectivity, forming a controlled stereogenic center at the allylic/propargylic

  通过使用在两个 N-芳基之一的邻位带有酚羟基的新型手性 N-杂环卡宾配体，开发了铜催化的末端炔烃与伯烯丙基磷酸酯的对映选择性烯丙基烷基化。该反应具有优异的 γ 分支区域选择性和高对映选择性，在烯丙基/炔丙基位置形成受控的立体中心。可以直接使用各种末端炔烃，包括甲硅烷基、脂肪族和芳香族炔烃，而无需对 C(sp)-H 键进行预金属化。根据使用异构仲烯丙基磷酸酯的实验结果，通过保留构型的 α-选择性取代反应得到支链产物，反应途径包括 1，
• Process for preparing optically active amino acid derivatives
  申请人：——

  公开号：US20030032814A1

  公开（公告）日：2003-02-13

  An optically active amino acid derivative is produced by N-protecting an optically active 3-haloalanine derivative followed by cyclization, or cyclizing this derivative followed by N-protection to thereby give an optically active N-protected-aziridine-2-carboxylic acid derivative which is protected by a benzenesulfonyl group substituted by nitro at the 2- and/or 4-positions and then treating this product with an organic metal reagent, or by N-protecting an optically active 3-haloalanine derivative to thereby give N-protected-aziridine-2-carboxylic acid which is protected by a benzenesulfonyl group substituted by nitro at the 2- and/or 4-positions and then treating this product with an organic metal reagent. According to this process, natural and unnatural optically active amino acids can be produced from inexpensive materials by using simple procedures.

  通过对具有光学活性的3-卤丙氨酸衍生物进行N-保护，然后进行环化，或者对该衍生物进行环化，然后进行N-保护，从而得到一种具有光学活性的N-保护-环氧丙烯酸衍生物，该衍生物由在2-和/或4-位置取代的硝基的苯磺酰基保护，然后用有机金属试剂处理，或者通过对具有光学活性的3-卤丙氨酸衍生物进行N-保护，从而得到由在2-和/或4-位置取代硝基的苯磺酰基保护的N-保护-环氧丙烯酸，然后用有机金属试剂处理。根据这个过程，可以通过简单的程序从廉价原料中生产天然和非天然的光学活性氨基酸。
• Process for producing optically active amino acid derivatives
  申请人：Sugawara Masanobu

  公开号：US20050143586A1

  公开（公告）日：2005-06-30

  An optically active amino acid derivative is produced by N-protecting an optically active 3-haloalanine derivative followed by cyclization, or cyclizing this derivative followed by N-protection to thereby give an optically active N-protected-aziridine-2-carboxylic acid derivative which is protected by a benzenesulfonyl group substituted by nitro at the 2- and/or 4-positions and then treating this product with an organic metal reagent, or by N-protecting an optically active 3-haloalanine derivative to thereby give N-protected-aziridine-2-carboxylic acid which is protected by a benzenesulfonyl group substituted by nitro at the 2- and/or 4-positions and then treating this product with an organic metal reagent. According to this process, natural and unnatural optically active amino acids can be produced from inexpensive materials by using simple procedures.

  通过N-保护光学活性3-卤代丙氨酸衍生物后进行环化，或通过环化此衍生物后进行N-保护，从而得到光学活性的N-保护的环氧丙烷-2-羧酸衍生物，该衍生物由在2-和/或4-位置上取代硝基的苯磺酰基保护，然后用有机金属试剂处理；或通过N-保护光学活性3-卤代丙氨酸衍生物，以得到由在2-和/或4-位置上取代硝基的苯磺酰基保护的环氧丙烷-2-羧酸，然后用有机金属试剂处理。根据此过程，可以使用简单的程序从廉价材料中生产天然和非天然的光学活性氨基酸。
• PROCESSES FOR PREPARING OPTICALLY ACTIVE AMINO ACID DERIVATIVES
  申请人：Kaneka Corporation

  公开号：EP1179530A1

  公开（公告）日：2002-02-13

  An optically active amino acid derivative is produced by N-protecting an optically active 3-haloalanine derivative followed by cyclization, or cyclizing this derivative followed by N-protection to thereby give an optically active N-protected-aziridine-2-carboxylic acid derivative which is protected by a benzenesulfonyl group substituted by nitro at the 2- and/or 4-positions and then treating this product with an organic metal reagent, or by N-protecting an optically active 3-haloalanine derivative to thereby give N-protected-aziridine-2-carboxylic acid which is protected by a benzenesulfonyl group substituted by nitro at the 2- and/or 4-positions and then treating this product with an organic metal reagent. According to this process, natural and unnatural optically active amino acids can be produced from inexpensive materials by using simple procedures.

  通过对具有光学活性的 3-卤丙氨酸衍生物进行 N 保护，然后进行环化，或对该衍生物进行环化，然后进行 N 保护，从而得到具有光学活性的 N 保护-氮丙啶-2-羧酸衍生物，该衍生物在 2-和/或 4-位受到被硝基取代的苯磺酰基的保护，然后用有机金属试剂处理该产物、或对具有光学活性的 3-卤丙氨酸衍生物进行 N 保护，从而得到 N 保护氮丙啶-2-羧酸，该氮丙啶-2-羧酸在 2-和/或 4-位上受到被硝基取代的苯磺酰基的保护，然后用有机金属试剂处理该产物。 根据这一工艺，可以通过简单的程序从廉价的材料中生产出天然和非天然的光学活性氨基酸。
• US6720449B2
  申请人：——

  公开号：US6720449B2

  公开（公告）日：2004-04-13