N-Boc-S-trifluoromethyl-L-homocysteine | 201870-90-8

• 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: N-Boc-S-trifluoromethyl-L-homocysteine
• 英文别名: (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-(trifluoromethylsulfanyl)butanoic acid
• CAS: 201870-90-8
• 化学式: C₁₀H₁₆F₃NO₄S
• 分子量: 303.303
• InChiKey: SXGHUJFMBJJFEU-LURJTMIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  101
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-Boc-S-trifluoromethyl-L-homocysteine 在 1-羟基苯并三唑 、 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 19.0h， 生成 (S)-2-[(S)-2-((S)-2-Formylamino-4-trifluoromethylsulfanyl-butyrylamino)-4-methyl-pentanoylamino]-3-phenyl-propionic acid methyl ester
  参考文献：
  名称：

  Syntheses of and chemotactic responses elicited by fMet-Leu-Phe analogs containing difluoro- and trifluoromethionine

  摘要：

  N-Formylmethionylleucylphenylalanine tripeptides containing either L-difluoro-or L-trifluoromethionine as replacements for methionine were synthesized by solution methods. The fluorinated peptides were found to have potent chemoattractant activities on human neutrophils. Ab initio calculations were utilized to further understand the changes in electronic properties of the methionine side chain upon fluorination. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)10134-2
• 作为产物：
  描述：

  三氟碘甲烷 、 N,N'-di(tert-butoxycarbonyl)-L-homocystine 在 氨 、 sodium 、 柠檬酸 作用下， 以 水 为溶剂， 反应 0.33h， 以70%的产率得到N-Boc-S-trifluoromethyl-L-homocysteine
  参考文献：
  名称：

  Simple preparation of trifluoromethionine and derivatives thereof

  摘要：

  公开了一种用于简单制备三氟甲硫氨酸及其类似物三氟甲基半胱氨酸、氟烷基同型半胱氨酸和氟烷基半胱氨酸以及它们的衍生物的方法。这些化合物是候选药物化合物或候选药物化合物的原料。具体地，通过在液氨中向光学活性或消旋半胱氨酸或半胱氨酸中添加金属钠，然后在伯奇还原条件下进一步添加氟烷基碘，可以简单方便地直接制备三氟甲硫氨酸、三氟甲基半胱氨酸、氟烷基同型半胱氨酸或氟烷基半胱氨酸，而无需经过同型半胱氨酸或半胱氨酸。

  公开号：

  US20110015433A1

文献信息

• NOVEL TRIHALOMETHIONINE DERIVATIVE AND PHARMACEUTICAL PRODUCT CONTAINING THE SAME
  申请人：Nozaki Tomoyoshi

  公开号：US20100076224A1

  公开（公告）日：2010-03-25

  A compound represented by the formula (I) is used as an active ingredient in a medicament for treatment or prevention of infectious diseases caused by protozoa or bacterium. X represents halogen, Z represents —(CH 2 ) m — wherein m is an integer of 1-5, and R represents one of the following (i)-(v): (i) hydrogen n represents an integer of 0-5, R 1 's independently represent hydrogen, halogen, alkoxy having 1-5 carbon atoms or alkyl having 1-5 carbon atoms. R 2 's independently represent hydrogen, halogen, alkoxy having 1-5 carbon atoms or alkyl having 1-5 carbon atoms. (iv) alkyl having 1-5 carbon atoms, (v) hydroxyalkyl having 1-5 carbon atoms.

  公式（I）代表的化合物被用作药物的活性成分，用于治疗或预防由原虫或细菌引起的传染病。X代表卤素，Z代表—(CH2)m—，其中m是1-5的整数，R代表以下之一：(i) 氢代表0-5的整数，R1独立代表氢、卤素、具有1-5个碳原子的烷氧基或具有1-5个碳原子的烷基。R2独立代表氢、卤素、具有1-5个碳原子的烷氧基或具有1-5个碳原子的烷基。(iv) 具有1-5个碳原子的烷基，(v) 具有1-5个碳原子的羟基烷基。
• Trihalomethionine derivative and pharmaceutical product containing the same
  申请人：National University Corporation, Gunma University

  公开号：US07868206B2

  公开（公告）日：2011-01-11

  A compound represented by the formula (I) is used as an active ingredient in a medicament for treatment or prevention of infectious diseases caused by protozoa or bacterium. X represents halogen, Z represents —(CH2)m— wherein m is an integer of 1-5, and R represents one of the following (i)-(v): (i) hydrogen n represents an integer of 0-5, R1's independently represent hydrogen, halogen, alkoxy having 1-5 carbon atoms or alkyl having 1-5 carbon atoms. R2's independently represent hydrogen, halogen, alkoxy having 1-5 carbon atoms or alkyl having 1-5 carbon atoms. (iv) alkyl having 1-5 carbon atoms, (v) hydroxyalkyl having 1-5 carbon atoms.

  公式（I）所代表的化合物被用作治疗或预防由原虫或细菌引起的传染病的药物的活性成分。其中，X代表卤素，Z代表—（CH2）m—，其中m是1-5的整数，R代表以下之一（i）-（v）：（i）氢，表示0-5的整数，R1独立地表示氢，卤素，具有1-5个碳原子的烷氧基或具有1-5个碳原子的烷基。R2独立地表示氢，卤素，具有1-5个碳原子的烷氧基或具有1-5个碳原子的烷基。（iv）具有1-5个碳原子的烷基，（v）具有1-5个碳原子的羟基烷基。
• Robust synthesis of trifluoromethionine and its derivatives by reductive trifluoromethylation of amino acid disulfides by CF3I/Na/Liq.NH3 system
  作者：Hiroyuki Yasui、Takeshi Yamamoto、Etsuko Tokunaga、Norio Shibata

  DOI：10.1016/j.jfluchem.2011.01.001

  日期：2011.3

  We disclose the reductive trifluoromethylation of chemically stable homocystine and cystine to provide corresponding trifluoromethyl ethers by the CF3I/Na/Liq.NH3 system. Both non-protected and protected homocystines can be nicely converted into trifluoromethylated methionines under the same condition. The method described offers a robust synthesis of pharmaceutically important trifluoromethionine, suitable for multigram synthesis. Pentafluoroethylation of homocystine was also achieved by the CF3CF2I/Na/Liq.NH3 system. (C) 2011 Elsevier B.V. All rights reserved.
• US7868206B2
  申请人：——

  公开号：US7868206B2

  公开（公告）日：2011-01-11
• Simple preparation of trifluoromethionine and derivatives thereof
  申请人：SHIBATA Norio

  公开号：US20110015433A1

  公开（公告）日：2011-01-20

  Disclosed is a process for the simple preparation of trifluoromethionine, its analogs trifluoromethylcysteine, fluoroalkylhomocysteines, and fluoroalkylcysteines, and derivatives of them. These compounds are drug-candidate compounds or raw materials of drug-candidate compounds. Specifically, trifluoromethionine, trifluoromethylcysteine, a fluoroalkylhomocysteine, or a fluoroalkylcysteine is simply and conveniently prepared directly without passing through homocysteine or cysteine by adding metallic sodium to an optically active or racemic homocystine or cystine in liquid ammonia and further adding a fluoroalkyl iodide thereto under Birch reduction conditions.

  公开了一种用于简单制备三氟甲硫氨酸及其类似物三氟甲基半胱氨酸、氟烷基同型半胱氨酸和氟烷基半胱氨酸以及它们的衍生物的方法。这些化合物是候选药物化合物或候选药物化合物的原料。具体地，通过在液氨中向光学活性或消旋半胱氨酸或半胱氨酸中添加金属钠，然后在伯奇还原条件下进一步添加氟烷基碘，可以简单方便地直接制备三氟甲硫氨酸、三氟甲基半胱氨酸、氟烷基同型半胱氨酸或氟烷基半胱氨酸，而无需经过同型半胱氨酸或半胱氨酸。