4-(benzylthio)butanal | 133549-39-0

• 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: 4-(benzylthio)butanal
• 英文别名: 4-benzylsulfanylbutanal
• CAS: 133549-39-0
• 化学式: C₁₁H₁₄OS
• 分子量: 194.298
• InChiKey: OJKZYQQIJCPRTA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  42.4
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  4-(benzylthio)butanal 在 sodium cyanoborohydride 、 N,N-二异丙基乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.17h， 生成 (S)-2-[(4-Benzylsulfanyl-butyl)-trimethylsilanyl-amino]-4-methylsulfanyl-butyric acid
  参考文献：
  名称：

  Building units for N-backbone cyclic peptides. Part 4.1 Synthesis of protected Nα-functionalized alkyl amino acids by reductive alkylation of natural amino acids

  摘要：

  报道了一种通过天然氨基酸的还原烷基化合成保护的Nα-(γ-Y-烷基)氨基酸(Y为硫、氨基或羧基基团)及相关化合物的新方法。这些新型氨基酸作为合成骨架环肽的构建单元，在α-氨基位置通过叔丁氧羰基(Boc)或9-芴甲氧羰基(Fmoc)进行正交保护，并使用三甲基硅烷临时保护，以便通过固相肽合成法将其并入肽链中。

  DOI：

  10.1039/a608389g
• 作为产物：
  描述：

  benzyl(4,4-diethoxybutyl)sulfane 在 盐酸 、 水 作用下， 以 丙酮 为溶剂， 生成 4-(benzylthio)butanal
  参考文献：
  名称：

  仿生四氧嘧啶催化的分子内氧化还原反应与O 2：一锅原子经济合成亚磺酰基官能化苯并咪唑

  摘要：

  鉴于在各种仿生需氧氧化中必须使用牺牲性还原剂，通过巧妙地结合底物硫化物和牺牲性还原剂，开发了用于一锅原子经济合成亚磺酰基官能化苯并咪唑的四氧嘧啶催化的有氧氧化还原系统。除了对环境无害的分子氧以外，这种温和且无过渡金属的方案无需额外的牺牲试剂即可进行两次氧化。

  DOI：

  10.1016/j.tetlet.2020.152688

文献信息

• 2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane: New masked lithium bishomoenolates in the synthesis of bifunctionalized compounds
  作者：Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4039(00)97465-3

  日期：——

  2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane (2) are prepaned by lithiation of the corresponding chlorinated precursors with lithium naphthalenide at −78°C. The reaction of these masked bishomoenolates with different electrophiles yields the expected monoprotected functional carbonyl compounds (3–12), which can be easily deprotected under acid conditions.

  通过在-78℃下用萘二甲酸锂对相应的氯化前体进行锂化来预沉积2-（3-Lithiopropyl）-和2-（3-lithiopropyl）-2-甲基-1,3-二氧戊环（2）。这些被掩盖的双歧烯酸酯与不同的亲电试剂的反应产生了预期的单保护的羰基官能化合物（3-12），在酸性条件下可以很容易地对其进行脱保护。
• C,C-coupling with sulfur-stabilized carbanions — 6. Preparation and electrophilic substitution of 1-[3-methyl-2-(2-thiolanylthio)-butyl]piperidine and dethioacetalization of semicyclic dithioacetals,
  作者：C Birk

  DOI：10.1016/0040-4020(96)00757-0

  日期：1996.9.23

  dithioacetals 12 – 15 are converted into the corresponding carbonyl compounds with [bis(trifluoroacetoxy)iodo]benzene (PIFA). Phenyl dichlorophosphate (PDCP) in the presence of sodium iodide and DMF is found to be a reagent for selective cleavage of the exocyclic CS bond. By using DOWEX 50W and paraformaldehyde in acetone/water a cleavage of both acetalic CS bonds is achieved in certain cases.

  通过对映体纯的1-（2-巯基-3-甲基丁基）哌啶（6）从L-缬氨酸获得1- [3-甲基-2-（2-硫代丙氨硫基）丁基]哌啶（8）。通过柱色谱分离非对映异构体，并研究碳负离子8a与亲电试剂的反应。半环二硫缩醛12-15与[双（三氟乙酰氧基）碘]苯（PIFA）转化为相应的羰基化合物。发现在碘化钠和DMF存在下的二氯磷酸苯酯（PDCP）是选择性裂解环外CS键的试剂。在某些情况下，通过在丙酮/水中使用DOWEX 50W和低聚甲醛，可以实现两个缩醛CS键的裂解。
• Chiral-at-Ruthenium-SEGPHOS Catalysts Display Diastereomer-Dependent Regioselectivity: Enantioselective Isoprene-Mediated Carbonyl <i>tert</i>-Prenylation via Halide Counterion Effects
  作者：Jonathan Z. Shezaf、Catherine G. Santana、Connor Saludares、Edward S. Briceno、Ken Sakata、Michael J. Krische

  DOI：10.1021/jacs.3c06734

  日期：2023.8.23

  correlation between metal-centered stereogenicity and regioselectivity in a catalytic process is described. Alternate pseudo-diastereomeric chiral-at-ruthenium complexes of the type RuX(CO)[η3-prenyl][(S)-SEGPHOS] form in a halide-dependent manner and display divergent regioselectivity in catalytic C–C couplings of isoprene to alcohol proelectrophiles via hydrogen autotransfer. Whereas the chloride-bound ruthenium-SEGPHOS

  描述了催化过程中金属中心立体异构性和区域选择性之间的第一个相关性。 RuX(CO)[η 3 -prenyl][( S )-SEGPHOS] 类型的替代假非对映手性钌络合物以卤化物依赖性方式形成，并在异戊二烯与异戊二烯的催化 C-C 偶联中表现出不同的区域选择性。醇亲电体通过氢自转移。氯化物结合的钌-SEGPHOS络合物更倾向于卤化物和羰基配体之间的反式关系，并提供羰基仲异戊二烯化的产物，而碘化物结合的钌-SEGPHOS络合物更倾向于卤化物和羰基配体之间的顺式关系，并提供羰基仲异戊二烯化的产物。羰基叔异戊二烯化的产物。通过31 P NMR 和 X 射线衍射对溶液和固相中的氯化物和碘化物结合的钌-SEGPHOS 配合物进行了表征。碘化物结合催化剂的密度泛函理论计算暗示了科廷-哈米特型场景，其中仲异戊二烯和叔异戊二烯钌配合物的平衡混合物中醛配位的过渡态是速率和产物决定的。因此，对以金属为中心的非
• 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.
• RAMON, DIEGO J.;YUS, MIGUEL, TETRAHEDRON LETT., 31,(1990) N6, C. 3763-3766
  作者：RAMON, DIEGO J.、YUS, MIGUEL

  DOI：——

  日期：——