1-amino-1-(S)-carboxy-5-(t-butoxycarbonyl amino)-3-pentyne | 77369-64-3

• 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-amino-1-(S)-carboxy-5-(t-butoxycarbonyl amino)-3-pentyne
• 英文别名: 1-amino-1-(S)-carboxy-5-(t-butoxycarbonylamino)-3-pentyne；(2S)-2-amino-6-[(2-methylpropan-2-yl)oxycarbonylamino]hex-4-ynoic acid
• CAS: 77369-64-3
• 化学式: C₁₁H₁₈N₂O₄
• 分子量: 242.275
• InChiKey: VGPMPXRXFKMHQU-QMMMGPOBSA-N

物化性质

• 沸点：
  422.4±45.0 °C(Predicted)
• 密度：
  1.185±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.1
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  102
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1-amino-1-(S)-carboxy-5-(t-butoxycarbonyl amino)-3-pentyne 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 三聚氯氰 、 氢气 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 25.0 ℃ 、47.33 kPa 条件下， 反应 71.0h， 生成 (S)-6-{[(1,1-dimethylethyl)oxy]carbonyl}-2-(p-tolylsulfonyl)aminohexan-4,4,5,5-3H-oyl chloride
  参考文献：
  名称：

  The novel synthesis of the protease inhibitor (S)-1-chloro-3-[(p-tolylsulfonyl)amino]-7-amino-2-[5,5,6,6-3H]heptanone ([3H]TLCK) labeled to high specific activity with tritium

  摘要：

  The protease inhibitor (S)-1-chloro-3-[(p-tolylsulfonyl)amino][5,5,6,6-H-3]heptanone ([H-3]TLCK) was prepared in an overall 41% radiochemical yield with a specific activity of 1.6 Ci/mmol in a 'one-pot' 3 step sequence beginning with (S)-6-[[(1,1-dimethylethyl)oxy]carbonyl]-2-(p-tolylsulfonyl)amino[4,4,5,5-H-3]hexanoic acid. The latter was prepared with a specific activity of 123 Ci/mmol in a 3 step sequence beginning with the stereospecific enzymatic hydrolysis of the commercially available racemic 2-acetylamino-6-[[(1,1-dimethylethyl)-oxy]carbonyl]aminohexan-4-ynoic acid, followed by tosylation and then palladium catalyzed reduction of the triple bond under tritium.

  DOI：

  10.1002/(sici)1099-1344(199705)39:5<379::aid-jlcr981>3.0.co;2-i
• 作为产物：
  描述：

  4-氯-2-丁炔基氨基甲酸叔丁酯 在 氢氧化钾 、 porcine kidney acylase I 、 cobalt(II) chloride 作用下， 以 1,4-二氧六环 、 乙醇 为溶剂， 反应 62.0h， 生成 1-amino-1-(S)-carboxy-5-(t-butoxycarbonyl amino)-3-pentyne
  参考文献：
  名称：

  Synthesis of mono- and di-acylated L-2,6-diamino-4-hexynoic acid potential derivatives for preparation of 3H-labelled lysine containing peptides

  摘要：

  DOI：

  10.1016/s0040-4039(00)92878-8

文献信息

• The synthesis of precursors of labelled neuropeptides
  作者：J. W. van Nispen、W. A. A. J. Bijl、A. M. M. Hendrix、H. M. Greven

  DOI：10.1002/recl.19831020505

  日期：——

  Modified amino acids which can serve as precursors in the synthesis of tritium-labelled peptides were prepared and incorporated into biologically active peptides. Thus, p-iodophenylalanine was incorporated at position 4 of H-Met(O2)-Glu-His-Phe-D-Lys-Phe-OH (Org 2766) and in des-Tyr1-γ-endorphin. As a second labelling site, the precursor of L-leucine, L-methallylglycine, was incorporated in both des-Tyr1-γ-endorphin

  制备了可在the标记肽合成中用作前体的修饰氨基酸，并将其掺入生物活性肽中。因此，将对碘苯丙氨酸引入H-Met（O 2）-Glu-His-Phe-D-Lys-Phe-OH（Org 2766）的4位和des-Tyr 1 -γ-内啡肽中。作为第二个标记位点，将L-亮氨酸的前体L-甲基烯丙基甘氨酸掺入了两个des-Tyr 1中-γ-内啡肽和较短的去脑啡肽-γ-内啡肽。最后，Org 2766（D-Lys）和去脑啡肽-γ-内啡肽（L-Lys）中的赖氨酸残基被其类似物2,6-二氨基-4-己酸取代。前体肽通过片段缩合方法合成。除了不能防止甲硫氨酸残基的部分脱硫的含甲基烯丙基甘氨酸的des-Tyr 1 -γ-内啡肽外，这些肽可以通过催化还原转化成它们各自的母体化合物。
• Antihypertensive compounds
  申请人：Schering Corporation

  公开号：US04826816A1

  公开（公告）日：1989-05-02

  Antihypertensive compounds with angiotensin-converting enzyme inhibitory activity and diuretic activity are disclosed. Such compounds are useful in the treatment of cardiovascular disorders, especially hypertension and congestive heart failure, and are useful in the treatment of glaucoma.

  抗高血压化合物具有抑制血管紧张素转换酶活性和利尿作用。这些化合物在治疗心血管疾病，特别是高血压和充血性心力衰竭方面很有用，并且在青光眼的治疗中也很有用。
• Antiglaucoma agents
  申请人：Schering Corporation

  公开号：US04885293A1

  公开（公告）日：1989-12-05

  Pharmaceutical compositions and a method for reducing intraocular pressure by topically applying a carboxyalkyl dipeptide are disclosed.

  揭示了一种通过局部涂抹羧基烷基二肽来降低眼内压力的药物组合物和方法。
• Antihypertensive compounds having both diuretic and angiotensin
  申请人：Schering Corporation

  公开号：US04556655A1

  公开（公告）日：1985-12-03

  Antihypertensive compounds with angiotensin-converting enzyme inhibitory activity and diuretic activity are disclosed. Such compounds are useful in the treatment of cardiovascular disorders, especially hypertension and congestive heart failure, and are useful in the treatment of glaucoma.

  抗高血压化合物具有抑制血管紧张素转化酶活性和利尿作用。这些化合物在治疗心血管疾病，特别是高血压和充血性心力衰竭方面非常有用，并且在青光眼的治疗中也有用。
• CARBOXYALKYLDIPEPTIDES, THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
  申请人：SCHERING CORPORATION

  公开号：EP0195817A1

  公开（公告）日：1986-10-01