4-(benzylthio)-1-phenylbutan-1-one | 133578-18-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(benzylthio)-1-phenylbutan-1-one
• 英文别名: 4-Benzylsulfanyl-1-phenylbutan-1-one
• CAS: 133578-18-4
• 化学式: C₁₇H₁₈OS
• mdl: MFCD12493881
• 分子量: 270.395
• InChiKey: TWENXAGHLQXDEK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  19
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.235
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  二苄基二硫 在 盐酸 作用下， 以 四氢呋喃 为溶剂， 反应 2.0h， 生成 4-(benzylthio)-1-phenylbutan-1-one
  参考文献：
  名称：

  Masked lithium bishomoenolates: useful intermediates in organic synthesis

  摘要：

  The lithiation of the chloro ketals 9 with lithium naphthalenide at -78-degrees-C led to the corresponding masked lithium bishomoenolates 4, which are stable species under these conditions and react with different electrophilic reagents (H2O, D2O, i-PrCHO, PhCHO, MeCOEt, (activated CH2)4CO, (activated CH2)5CO, (activated CH2)7CO, PhCOMe, c-C3H5COPh, PhCN, HCONMe2, PrCO activated N(CH2)4, PhCO activated N(CH2)4, PhCOCl, EtOCOCl, PhCHNPh, and (PhCH2S)2) to give, after hydrolysis with water, the corresponding bifunctionalized compounds 10a-22a, 10b-22b, and 10c-15c. When alkyl halides were used as electrophiles the reaction failed. In the presence of a catalytic amount of the complex CuBr.Me2S, the same reaction with alpha,beta-unsaturated ketones (methyl vinyl ketone or 2-cyclohexanone) yielded the expected products of a 1,4-addition 25a-c and 26b. The deprotection of the masked carbonyl group was easily done by treatment with 2 N hydrochloric acid in THF, so as examples, compounds 27a-29a, 30b, 31b, 32c, and 33c were isolated. The transformation of hemiacetals of the type 27a into substituted tetrahydropyrans was carried out by means of compounds of the type R3SiNu (Nu = H, allyl, CN) in the presence of BF3, so products 34a-41a, 42b, and 43b were prepared. Finally, the in situ oxidation of the deprotected products of the type 27a-arising from the reaction of bishomoenolate 4a with carbonyl compounds-with Jones reagent (for ketones derivatives) or PCC (for aldehydes derivatives) led to the corresponding delta-lactones 44-57.

  DOI：

  10.1021/jo00012a012

文献信息

• Catalytic base-controlled regiodivergent heteronucleophilic hydrofunctionalization of β,γ-unsaturated amides
  作者：Yao Zhao、Jiacheng Rui、Qiang Du、Rizhi Chen、Ying Zhan、Xintao Zheng、Xiaojin Wu

  DOI：10.1039/d1cc03440e

  日期：——

  A catalytic base-controlled regiodivergent and chemoselective nucleophilic hydrofunctionalization of both terminal and internal β,γ-unsaturated amides was reported for the first time.

  首次报道了一种催化碱控制的基团分歧和化学选择性亲核水合功能化，可同时作用于末端和内部β,γ-不饱和酰胺。
• Manganese-catalyzed regiospecific sp³C–S bond formation through C–C bond cleavage of cyclobutanols
  作者：Rongguo Ren、Zhen Wu、Chen Zhu

  DOI：10.1039/c6cc01843b

  日期：——

  A manganese-catalyzed regioselective sp3 C-S bond formation through C-C bond cleavage of cyclobutanols is described. A variety of primary and secondary alkyl thioethers are efficiently prepared under mild reaction conditions....

  描述了通过环丁醇的CC键裂解形成的锰催化的区域选择性sp3 CS键。在温和的反应条件下可以有效地制备各种伯和仲烷基硫醚。
• Electrophotochemical Ce-Catalyzed Ring-Opening Functionalization of Cycloalkanols under Redox-Neutral Conditions: Scope and Mechanism
  作者：Zhaoliang Yang、Dali Yang、Jianye Zhang、Chenyu Tan、Jiajun Li、Shengchun Wang、Heng Zhang、Zhiliang Huang、Aiwen Lei

  DOI：10.1021/jacs.2c05520

  日期：2022.8.3

  alcohols is gaining increasing interest in organic synthesis and biomass conversion. In particular, the development of redox-neutral catalytic methods with cheap catalysts and clean energy is of utmost interest. In this work, we report a versatile redox-neutral method for the ring-opening functionalization of cycloalkanols by electrophotochemical (EPC) cerium (Ce) catalysis. The EPC-Ce-enabled catalysis

  醇中 C-C 键的选择性裂解和功能化在有机合成和生物质转化中越来越受到关注。特别是开发具有廉价催化剂和清洁能源的氧化还原中性催化方法是最受关注的。在这项工作中，我们报告了一种通用的氧化还原中性方法，用于通过电光化学 (EPC) 铈 (Ce) 催化对环烷醇进行开环功能化。启用 EPC-Ce 的催化允许切割具有不同环尺寸的环烷醇，同时耐受广泛的官能团。值得注意的是，在氯化物作为抗衡阴离子和电解质存在的情况下，该方案选择性地导致形成 C-CN、C-C、C-S 或 C-肟键，而不是在 β-断裂后形成 C-卤化物键。初步机理研究表明，氧化还原活性 Ce 催化剂可以通过电氧化和光还原来调节，从而避免使用外部氧化剂。光谱表征（循环伏安法、UV-vis、电子顺磁共振和 X 射线吸收精细结构）表明了这种转化的 Ce(III)/Ce(IV) 催化途径，其中涉及 Ce(IV)-醇盐.
• RAMON, DIEGO J.;YUS, MIGUEL, J. ORG. CHEM., 56,(1991) N2, C. 3825-3831
  作者：RAMON, DIEGO J.、YUS, MIGUEL

  DOI：——

  日期：——
• Masked lithium bishomoenolates: useful intermediates in organic synthesis
  作者：Diego J. Ramon、Miguel Yus

  DOI：10.1021/jo00012a012

  日期：1991.6

  The lithiation of the chloro ketals 9 with lithium naphthalenide at -78-degrees-C led to the corresponding masked lithium bishomoenolates 4, which are stable species under these conditions and react with different electrophilic reagents (H2O, D2O, i-PrCHO, PhCHO, MeCOEt, (activated CH2)4CO, (activated CH2)5CO, (activated CH2)7CO, PhCOMe, c-C3H5COPh, PhCN, HCONMe2, PrCO activated N(CH2)4, PhCO activated N(CH2)4, PhCOCl, EtOCOCl, PhCHNPh, and (PhCH2S)2) to give, after hydrolysis with water, the corresponding bifunctionalized compounds 10a-22a, 10b-22b, and 10c-15c. When alkyl halides were used as electrophiles the reaction failed. In the presence of a catalytic amount of the complex CuBr.Me2S, the same reaction with alpha,beta-unsaturated ketones (methyl vinyl ketone or 2-cyclohexanone) yielded the expected products of a 1,4-addition 25a-c and 26b. The deprotection of the masked carbonyl group was easily done by treatment with 2 N hydrochloric acid in THF, so as examples, compounds 27a-29a, 30b, 31b, 32c, and 33c were isolated. The transformation of hemiacetals of the type 27a into substituted tetrahydropyrans was carried out by means of compounds of the type R3SiNu (Nu = H, allyl, CN) in the presence of BF3, so products 34a-41a, 42b, and 43b were prepared. Finally, the in situ oxidation of the deprotected products of the type 27a-arising from the reaction of bishomoenolate 4a with carbonyl compounds-with Jones reagent (for ketones derivatives) or PCC (for aldehydes derivatives) led to the corresponding delta-lactones 44-57.