3-benzylthio-3-methyl-1-butanol | 74252-98-5

• 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-benzylthio-3-methyl-1-butanol
• 英文别名: 3-methyl-3-thiobenzylbutan-1-ol；3-benzylsulfanyl-3-methyl-butan-1-ol；3-Benzylmercapto-3-methyl-butan-1-ol；3-Benzylsulfanyl-3-methylbutan-1-ol
• CAS: 74252-98-5
• 化学式: C₁₂H₁₈OS
• 分子量: 210.34
• InChiKey: ACDRIVGQSUNIQO-UHFFFAOYSA-N

物化性质

• 沸点：
  120-122 °C(Press: 0.3 Torr)
• 密度：
  1.052±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  45.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  3-benzylthio-3-methyl-1-butanol 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 生成 4-Benzylsulfanyl-4-methylpentanenitrile
  参考文献：
  名称：

  Fluorophore-Labeled S-Nitrosothiols

  摘要：

  A series of fluorophore-labeled S-nitrosothiols were synthesized, and their fluorescence enhancements upon removal of the nitroso (NO) group were evaluated either by transnitrosation or by photolysis. It was shown that, with a suitable alkyl linker, the fluorescence intensity of dansyl-labeled S-nitrosothiols could be enhanced up to 30-fold. The observed fluorescence enhancement was attributed to the intramolecular energy transfer from fluorophore to the SNO moiety. Ab initio density functional theory (DFT) calculations indicated that the "overlap" between the SNO moiety and the dansyl ring is favored because of their stabilizing interaction, which was in turn affected by both the length of the alkyl linker and the rigidity of the sulfonamide unit. In addition, one of the dansyl-labeled S-nitrosothiols was used to explore the kinetics of S-nitrosothiol/thiol transnitrosation and was evaluated as a fluorescence probe of S-nitrosothiol-bound NO transfer in human umbilical vein endothelial cells.

  DOI：

  10.1021/jo015658p
• 作为产物：
  描述：

  3-甲基-2-丁烯醛 在 (2S,4R)-2{[3,5-(CF₃)2C₆H₃]2CH(OTMS)}-4-TBSO-pyrrolidine 苯甲酸 、 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 24.5h， 以67%的产率得到3-benzylthio-3-methyl-1-butanol
  参考文献：
  名称：

  硫醇与α,β-不饱和醛的无溶剂有机催化不对称共轭加成

  摘要：

  硫醇与α,β-不饱和醛的高度对映选择性不对称共轭加成由新设计的无溶剂有机催化剂催化。

  DOI：

  10.1246/cl.2007.550

文献信息

• Sulfur participation in solvolysis involving four-membered ring intermediates
  作者：Ernest L. Eliel、William H. Pearson、Linda M. Jewell、Anthony G. Abatjoglou、William R. Kenan

  DOI：10.1016/s0040-4039(01)85465-4

  日期：1980.1

  Neighboring group participation via four-membered ring intermediates resulting in complete rearrangement occurs in the methanolysis of R1R2C(SCH2C6H5)CH2CH(R3)OTs when R1=R2=R3=Me and when R1=R2=Me, R3=H. No rearrangement is found for R1=R2=R3=H or R1=R2=H, R3=Me. The case of R1=Me, R2=R3=H is intermediate.

  当R 1 = R 2 = R 3 = Me时，在R 1 R 2 C（SCH 2 C 6 H 5）CH 2 CH（R 3）OTs的甲醇分解中，经由四元环中间体的相邻基团参与导致完全重排。当R 1＝ R 2＝ Me时，R 3＝ H。对于R 1＝ R 2＝ R 3＝ H或R 1＝ R 2＝ H，R 3＝ Me ，没有发现重排。R 1 = Me，R 2的情况= R 3 = H是中间的。
• A novel tandem [4++2] cycloaddition–elimination reaction: 2-alkenyl-4,4-dimethyl-1,3-oxathianes as synthetic equivalents for α,β-unsaturated thioaldehydes
  作者：Shin-ichi Ohsugi、Kiyoharu Nishide、Manabu Node

  DOI：10.1016/s0040-4020(03)00179-0

  日期：2003.3

  The first tandem cationic [4(+)+2] polar cycloaddition-elimination reaction of 1-thia-1,3-butadienyl cations B with olefins to afford directly 3,4-dihydro-2H-thiopyrans D is described. The cations B were easily accessible by treatment of monothioacetals A, particularly the 2-alkenyl-4,4-dimethyl-1,3-oxathianes 1, with a hard Lewis acid. In this novel reaction, 2-alkenyl-4,4-dimethyl-1,3-oxathianes were utilized as synthetic equivalents for highly reactive alpha,beta-unsaturated thioaldehydes. The effect of geminal dimethyl substituents on the oxathianes 1 and the mechanistic aspect of the reaction are considered. The reaction's asymmetric version was also investigated using a chiral oxathiane 4 derived from (-)-(IR,2R,5R)-2-(I-mercapto-l-methylethyl)-5-methylcyclohexanol. Although the enantioselectivities were moderate, the whole process can be done under odorless conditions. (C) 2003 Elsevier Science Ltd. All rights reserved.
• Trippett, Journal of the Chemical Society, 1957, p. 1929
  作者：Trippett

  DOI：——

  日期：——
• JP2001335557A
  申请人：——

  公开号：JP2001335557A

  公开（公告）日：2001-12-04
• [EN] PEPTIDE DRUG CONJUGATES<br/>[FR] CONJUGUÉS PEPTIDES-MÉDICAMENTS
  申请人：EISAI R&D MAN CO LTD

  公开号：WO2017136769A1

  公开（公告）日：2017-08-10

  Embodiments provide protein-drug conjugates for treatment of cancer. Protein-drug conjugates may include protein-drug conjugates of Formula I: Ctx-L-Cp (I) or a pharmaceutically acceptable salt or solvate thereof, wherein: Ctx is chlorotoxin or a chlorotoxin analog; Cp is a cryptophycin amide, and L is a linker wherein the linker is bound to Ctx at an X2 moiety of the linker and at one of a lysine residue and the N-terminus of the chlorotoxin or chlorotoxin analog.