4-(2'-Methyl-1',3'-dithian-2'-yl)butanal | 128084-17-3

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫代缩醛
• 英文名称: 4-(2'-Methyl-1',3'-dithian-2'-yl)butanal
• 英文别名: 4-(2-Methyl-1,3-dithian-2-yl)butanal
• CAS: 128084-17-3
• 化学式: C₉H₁₆OS₂
• 分子量: 204.357
• InChiKey: LTXCSHLSHQUTNN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  12
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  67.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4-(2'-Methyl-1',3'-dithian-2'-yl)butanal 在 二氯乙基铝 作用下， 以 乙醚 为溶剂， 反应 2.28h， 生成 N-<(S)-1-tert-butyloxycarbonyl-2-methylpropyl>-(5S)-5-amino-3-methoxy-8-(2-methyl-1,3-dithian-2-yl)oct-2-enoic acid methyl ester
  参考文献：
  名称：

  Asymmetric aza Diels-Alder reactions of amino acid ester imines with Brassard's diene

  摘要：

  Imines 1 obtained from aromatic, aliphatic or functionalized aldehydes and valine tert-butyl ester undergo Lewis acid catalyzed hetero Diels-Alder reactions with Brassard's diene 2. The cycloadducts are formed in good to high yields and with diastereomer ratios of 92:8-97:3. For the removal of the chiral auxiliary group a new method was developed whose principle consists in the conversion of the amino acid alpha-C-atom into an acetalic center employing a Curtius rearrangement as the key step.

  DOI：

  10.1016/s0957-4166(00)80023-3
• 作为产物：
  描述：

  2-甲基-1,3-二噻烷 在 硫酸 作用下， 生成 4-(2'-Methyl-1',3'-dithian-2'-yl)butanal
  参考文献：
  名称：

  兔肌肉醛缩酶的立体特异性CC键形成-（+）-exo-brevicomin的化学合成

  摘要：

  （+）-（1 S，5 R，7 S）-Exo-brevicomin 9是西松树皮甲虫的性信息素，它是利用果糖1,6-二磷酸醛缩酶（EC 4.1。 2.13）从兔肌肉开始，以此作为建立目标绝对构型的关键步骤。

  DOI：

  10.1016/s0040-4039(00)94649-5

文献信息

• Expansion of Substrate Scope for Nitroxyl Radical/Copper-Catalyzed Aerobic Oxidation of Primary Alcohols: A Guideline for Catalyst Selection
  作者：Yusuke Sasano、Aoto Yamaichi、Ryota Sasaki、Shota Nagasawa、Yoshiharu Iwabuchi

  DOI：10.1248/cpb.c21-00043

  日期：2021.5.1

  acceptors. The optimum conditions identified herein were successful in the oxidation of various types of primary alcohols, including unprotected amino alcohols and divalent-sulfur-containing alcohols in good-to-high yields. Moreover, N-protected alaninol, an inefficient substrate in the nitroxyl radical/copper-catalyzed aerobic oxidation, was oxidized in good yield. On the basis of the optimization results

  已经确定了四种独特的最佳硝酰基自由基/铜盐/添加剂催化剂组合，以适应各种类型的伯醇有氧氧化为它们相应的醛的需要。有趣的是，较少的亲核催化剂对特定的伯烯丙基和炔丙基醇的氧化表现出较高的催化活性，以产生充当迈克尔能受体的α，β-不饱和醛。本文确定的最佳条件成功地以高至高收率氧化了各种类型的伯醇，包括未保护的氨基醇和含二价硫的醇。而且，N保护的丙氨醇是硝基氧基自由基/铜催化的需氧氧化中效率低下的底物，可以得到良好的氧化。根据最优化结果，已经建立了催化剂选择指南。 全尺寸图片
• Zinc-copper(I) chloride or -silver acetate promoted coupling reaction of 2-[(Trimethylsilyl)methyl]-3-chloro-3,3-difluoropropene with carbonyl compounds. Highly efficient access to 2,2-difluoro homoallyl alcohols
  作者：Takashi Ishihara、Seiji Miwatashi、Manabu Kuroboshi、Kiitiro Utimoto

  DOI：10.1016/s0040-4039(00)74490-x

  日期：1991.2

  2-[(Trimethylsilyl)methyl]-3-chloro-3,3-difluoropropene, readily prepared in two steps from methyl chlorodifluoroacetate and (trimethylsilyl)methylmagnesium chloride, is reduced to couple regioselectivity with a variety of carbonyl compounds in the presence of zinc-copper(I) chloride or -silver acetate to give 2,2-difluoro-3-[(trimethylsilyl)methyl]-3-buten-1-ol derivatives in good to excellent yields

  2-[（三甲基甲硅烷基）甲基] -3-氯-3,3-二氟丙烯可以很容易地从氯二氟乙酸甲酯和（三甲基甲硅烷基）甲基氯化镁分两步制备，在锌存在下还原成具有多种羰基化合物的区域选择性-氯化铜（I）或-乙酸银，以良好或优异的产率得到2，2-二氟-3-[（（三甲基甲硅烷基）甲基] -3-丁烯-1-醇衍生物。
• Stereospecific CC-bond formation with rabbit muscle aldolase - A chemoenzymatic synthesis of (+)-exo-brevicomin
  作者：M. Schultz、H. Waldmann、W. Vogt、H. Kunz

  DOI：10.1016/s0040-4039(00)94649-5

  日期：1990.1

  (+)-(1S,5R,7S)-Exo-brevicomin 9, a sex pheromone of the western pine bark beetle, is synthesized using an aldol reaction catalyzed by fructose-1,6-diphosphate aldolase (EC 4.1.2.13) from rabbit muscle as the key step by which the absolute configuration of the target is established.

  （+）-（1 S，5 R，7 S）-Exo-brevicomin 9是西松树皮甲虫的性信息素，它是利用果糖1,6-二磷酸醛缩酶（EC 4.1。 2.13）从兔肌肉开始，以此作为建立目标绝对构型的关键步骤。
• A facile access to bridged 1,2,4-trioxanes
  作者：Qi Zhang、Hong-Xia Jin、Yikang Wu

  DOI：10.1016/j.tet.2006.09.061

  日期：2006.12

  Bicyclo[3.2.1] type 1,2,4-trioxanes are readily synthesized from precursors that may form intramolecular hemiketals using UHP (H2O2-urea complex) as the source of the peroxy bond and p-TsOH or CSA as the catalyst. The ring closure through an intramolecular Michael addition occurred in a highly stereoselective way, giving only one diasteromer as shown by the NMR spectra. (c) 2006 Elsevier Ltd. All rights reserved.
• SCHULTZ, M.;WALDMANN, H.;VOGT, W.;KUNZ, H., TETRAHEDRON LETT., 31,(1990) N, C. 867-868
  作者：SCHULTZ, M.、WALDMANN, H.、VOGT, W.、KUNZ, H.

  DOI：——

  日期：——