1-(vinylsulfonyl)-L-proline t-butyl ester | 67157-78-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-(vinylsulfonyl)-L-proline t-butyl ester
• 英文别名: N-(vinylsulfonyl)-L-proline t-butyl ester；tert-butyl (2S)-1-ethenylsulfonylpyrrolidine-2-carboxylate
• CAS: 67157-78-2
• 化学式: C₁₁H₁₉NO₄S
• 分子量: 261.342
• InChiKey: RPOFHGROZUSZFM-VIFPVBQESA-N

物化性质

• 熔点：
  84-87 °C(Solv: ethyl ether (60-29-7); hexane (110-54-3))
• 沸点：
  346.9±52.0 °C(Predicted)
• 密度：
  1.20±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  72.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-(vinylsulfonyl)-L-proline t-butyl ester 在 ammonium hydroxide 、 水 、 三乙胺 、 三氟乙酸 作用下， 以 乙醚 为溶剂， 反应 2.0h， 生成 1-<(2-Mercaptoethyl)-sulfonyl>-L-prolin
  参考文献：
  名称：

  Angiotensin-converting enzyme inhibitors: importance of the amide carbonyl of mercaptoacyl amino acids for hydrogen bonding to the enzyme

  摘要：

  A series of mercaptoacyl amino acids and related compounds was synthesized and evaluated for inhibition of angiotensin-converting enzyme (ACE) in order to determine the nature and importance of the putative interaction between ACE and the amide moiety of inhibitors such as captopril (3-mercapto-2-methylpropanoyl-L-proline). It was concluded that the interaction involves a hydrogen bond from a donor site on ACE to the oxygen of the amide carbonyl. Compounds in which the amide moiety is replaced by other groups (ester, ketone, sulfonamide) capable of accepting a hydrogen bond are effective inhibitors, but compounds in which only the geometrical features of the amide are retained are ineffective inhibitors. The presence of an NH group is not necessary for effective inhibition. The activity of a series of mercaptoacyl cycloalkyl carboxylic acids parallels the activity of the isosteric series of mercaptoacyl imino acids.

  DOI：

  10.1021/jm00345a011
• 作为产物：
  描述：

  L-脯氨酸叔丁酯 在 三乙胺 作用下， 以 正己烷 、 二氯甲烷 、 2-氯乙烷磺酰氯 、 乙酸乙酯 为溶剂， 生成 1-(vinylsulfonyl)-L-proline t-butyl ester
  参考文献：
  名称：

  Mercaptoalkylsulfonyl proline and pipecolic acid and esters thereof

  摘要：

  具有一般公式## STR1 ##的Mercaptoalkylsulfonyl脯氨酸衍生物和相关化合物是作为降压剂有用的。

  公开号：

  US04070361A1

文献信息

• Orally effective anti-hypertensive agents
  申请人：University of Miami

  公开号：US04745124A1

  公开（公告）日：1988-05-17

  Novel thiolester compounds are disclosed which are orally effective angiotensin converting enzyme inhibitors useful in the treatment of mammalian hypertension. They have the formula, R.sub.1 -A.sub.1 -S-Z, wherein Z denotes -B-A.sub.2, R.sub.1 is H or an acyl group, A.sub.1 is a carboxylic acid containing at least one amino or imino -N-, A.sub.2 is a carboxylic acid containing at least one amino or imino -N- or a lower alkyl ester or amide thereof, B is a 2-4 carbon backbone chain in mercapto linkage to S which includes a carbonyl or sulfonyl group joined in carboxamido or sulfonamido linkage, respectively, to A.sub.2. Preferably A.sub.2 includes a 4-6 membered C-N ring or a 5 membered ring of one N, one S and 3 C atoms.

  披露了新型硫醇酯化合物，它们是口服有效的血管紧张素转化酶抑制剂，用于治疗哺乳动物的 hypertension。它们具有以下公式，R.sub.1 -A.sub.1 -S-Z，其中 Z 表示 -B-A.sub.2，R.sub.1 是 H 或一个酰基团，A.sub.1 是至少含有一个氨基或亚氨基 -N- 的羧酸，A.sub.2 是至少含有一个氨基或亚氨基 -N- 的羧酸或其低级烷基酯或酰胺，B 是一个 2-4 碳骨架链，通过巯基连接到 S，并包括一个碳酰基或磺酰基团，分别通过羧酰胺或磺酰胺连接到 A.sub.2。优选的是 A.sub.2 包含一个 4-6 成员的 C-N 环或一个由一个 N、一个 S 和 3 个 C 原子组成的 5 成员环。
• Chemo- and Regioselective Direct Functional Group Installation through Catalytic Hydroxy Group Selective Conjugate Addition of Amino Alcohols to α,β-Unsaturated Sulfonyl Compounds
  作者：Zhao Li、Ryo Yazaki、Takashi Ohshima

  DOI：10.1021/acs.orglett.6b01464

  日期：2016.7.15

  A chemoselective functional group installation through catalytic hydroxy group selective conjugate addition of amino alcohols to a variety of functionalized α,β-unsaturated sulfonyl derivatives was developed. Azide group installation for click chemistry and facile fluorescent labeling onto the less reactive hydroxy group demonstrated the synthetic utility of the present chemoselective catalysis. Moreover

  通过将氨基醇催化羟基选择性共轭加成到各种官能化的α，β-不饱和磺酰基衍生物上，开发了化学选择性官能团。用于点击化学的叠氮基装置和在反应性较低的羟基上的简便荧光标记证明了本化学选择性催化的合成效用。此外，首次实现了未保护的氨基二醇的化学和区域选择性反应。
• Mercaptoalkylsulfonyl proline and pipecolic acid and esters thereof
  申请人：E. R. Squibb & Sons, Inc.

  公开号：US04070361A1

  公开（公告）日：1978-01-24

  Mercaptoalkylsulfonyl proline derivatives and related compounds which have the general formula ##STR1## are useful as hypotensive agents.

  具有一般公式## STR1 ##的Mercaptoalkylsulfonyl脯氨酸衍生物和相关化合物是作为降压剂有用的。
• Angiotensin converting enzyme inhibitors
  申请人：UNIVERSITY OF MIAMI

  公开号：EP0036713A2

  公开（公告）日：1981-09-30

  Novel inhibitors of angiotensin converting enzyme having the general formula R-A-S-Z are disclosed as potent inhibitors of angiotensin converting enzyme and are useful anti-hypertensive agents.

  公开了通式为 R-A-S-Z 的新型血管紧张素转换酶抑制剂，它们是血管紧张素转换酶的强效抑制剂，也是有用的抗高血压药物。
• RYAN, JAMES W.;CHUNG, ALFRED
  作者：RYAN, JAMES W.、CHUNG, ALFRED

  DOI：——

  日期：——