(R)-cysteinol | 253438-36-7

• 分子结构分类: 有机化合物 - 有机氮化合物
• 英文名称: (R)-cysteinol
• 英文别名: (2R)-2-amino-3-propan-2-ylsulfanylpropan-1-ol
• CAS: 253438-36-7
• 化学式: C₆H₁₅NOS
• 分子量: 149.257
• InChiKey: XRRQFLOAIZZKMM-ZCFIWIBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  9
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  71.6
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1,2-双(2-碘乙氧基)乙烷 、 (R)-cysteinol 在 sodium carbonate 作用下， 以 乙腈 为溶剂， 以27%的产率得到(R)-2-(1',4'-dioxa-7'-azacyclononan-7'-yl)-3-isopropylthiopropan-1-ol
  参考文献：
  名称：

  含有衍生自手性氨基醇的 N,O-杂环的新型手性催化剂

  摘要：

  在将二乙基锌添加到苯甲醛中时，已检查了一系列新的含有不同尺寸 N,O-杂环的手性催化剂所发挥的对映选择性，苯甲醛用作模型反应。催化剂来源于天然氨基酸，遵循相对简单的程序，在一些情况下获得了极好的 ee 值。结果是互补的，因为 ee 在最终 1-苯基丙-1-醇的 98% (R) 至 94% (S) 过量范围内。分子力学计算表明，R 醇的产生可以通过类似于 Noyori 描述的机制来解释，其中 ZnEt2 仅与 N-C-C-OH 片段相互作用，而 S 对映异构体的形成需要直接亲本氨基酸的侧链和 N,O-杂环的参与。

  DOI：

  10.1002/(sici)1099-0690(199912)1999:12<3323::aid-ejoc3323>3.0.co;2-w
• 作为产物：
  描述：

  在 锂硼氢 作用下， 以 四氢呋喃 为溶剂， 生成 (R)-cysteinol
  参考文献：
  名称：

  Pyrimidinylpropenamides as antitumor agents. Analogs of the antibiotic sparsomycin

  摘要：

  A series of pyrimidinylpropenamides 9 and their oxidation products 10 was prepared, as analogues of sparsomycin (1), for antitumor evaluation. Syntheses involved condensation of the appropriate amino alcohol 5 with acid 8. The resulting sulfides 9 were then oxidized with NaIO4 or H2O2 to sulfoxides 10. Activity was studied in lymphocytic leukemia P-338 and KB cell culture. With the exception of the n-decyl analogue, all of the deoxygenated compounds 9 were inactive regardless of the stereochemical form. In the sulfoxide series 10, those compounds prepared with an L configuration at the asymmetric carbon were also inactive. The completely racemic sulfoxides, on the other hand, displayed substantial antitumor activity (ILS = 37-61% in P-388; ED50 = 1.2-2.4 mug/ml in KB) suggesting that both the presence of a sulfoxide moiety and a D configuration at the chiral carbon atom were structural requirements for a positive antitumor response. There appeared to be a large tolerance for the group substituted at the sulfoxide moiety, however.

  DOI：

  10.1021/jm00213a004

文献信息

• Pyrimidinylpropenamides as antitumor agents. Analogs of the antibiotic sparsomycin
  作者：Chie-Chang L. Lin、Ronald J. Dubois

  DOI：10.1021/jm00213a004

  日期：1977.3

  A series of pyrimidinylpropenamides 9 and their oxidation products 10 was prepared, as analogues of sparsomycin (1), for antitumor evaluation. Syntheses involved condensation of the appropriate amino alcohol 5 with acid 8. The resulting sulfides 9 were then oxidized with NaIO4 or H2O2 to sulfoxides 10. Activity was studied in lymphocytic leukemia P-338 and KB cell culture. With the exception of the n-decyl analogue, all of the deoxygenated compounds 9 were inactive regardless of the stereochemical form. In the sulfoxide series 10, those compounds prepared with an L configuration at the asymmetric carbon were also inactive. The completely racemic sulfoxides, on the other hand, displayed substantial antitumor activity (ILS = 37-61% in P-388; ED50 = 1.2-2.4 mug/ml in KB) suggesting that both the presence of a sulfoxide moiety and a D configuration at the chiral carbon atom were structural requirements for a positive antitumor response. There appeared to be a large tolerance for the group substituted at the sulfoxide moiety, however.
• New Chiral Catalysts ContainingN,O-Heterocycles Derived from Chiral Amino Alcohols
  作者：Olga Juanes、Juan Carlos Rodriguez-Ubis、Ernesto Brunet、Helmut Pennemann、Michael Kossenjans、Jürgen Martens

  DOI：10.1002/(sici)1099-0690(199912)1999:12<3323::aid-ejoc3323>3.0.co;2-w

  日期：1999.12

  a new series of chiral catalysts containing N,O-heterocycles of different sizes has been checked in the addition of diethylzinc to benzaldehyde, which was used as a model reaction. The catalysts were derived from natural amino acids, following a relatively simple procedure, and in several cases excellent ee values were obtained. The results were complementary since ee's ranged from 98% (R) to 94% (S)

  在将二乙基锌添加到苯甲醛中时，已检查了一系列新的含有不同尺寸 N,O-杂环的手性催化剂所发挥的对映选择性，苯甲醛用作模型反应。催化剂来源于天然氨基酸，遵循相对简单的程序，在一些情况下获得了极好的 ee 值。结果是互补的，因为 ee 在最终 1-苯基丙-1-醇的 98% (R) 至 94% (S) 过量范围内。分子力学计算表明，R 醇的产生可以通过类似于 Noyori 描述的机制来解释，其中 ZnEt2 仅与 N-C-C-OH 片段相互作用，而 S 对映异构体的形成需要直接亲本氨基酸的侧链和 N,O-杂环的参与。