2,2,2-Trichloro-N-[(3aR,5S,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetamide | 850359-60-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,2,2-Trichloro-N-[(3aR,5S,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetamide
• 英文别名: N-[(3aR,5S,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-6-ethenyl-2,2-dimethyl-5,6a-dihydro-3aH-furo[2,3-d][1,3]dioxol-6-yl]-2,2,2-trichloroacetamide
• CAS: 850359-60-3
• 化学式: C₁₆H₂₂Cl₃NO₆
• 分子量: 430.713
• InChiKey: MDRASAMJYLGWDQ-IOQXRXCXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  75.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,2,2-Trichloro-N-[(3aR,5S,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetamide 在 sodium tetrahydroborate 、 高碘酸 作用下， 以 乙醇 、 乙酸乙酯 为溶剂， 生成 2,2,2-Trichloro-N-((3aR,5S,6S,6aR)-5-hydroxymethyl-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-acetamide
  参考文献：
  名称：

  One-Pot Transformation of Trichloroacetamide into Readily Deprotectable Carbamates

  摘要：

  A trichloroacetamide group was converted to an isocyanate, which was in situ captured by a variety of alcohols in the presence of CuCl and n-BuN4Cl to afford the corresponding carbamates. The scope and limitation of this transformation are also described.

  DOI：

  10.1021/ol061123c
• 作为产物：
  描述：

  1,2:5,6-二-o-异亚丙基-alpha-d-ribo-3-己呋喃核糖 在 二异丁基氢化铝 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 甲苯 、 xylene 为溶剂， 生成 2,2,2-Trichloro-N-[(3aR,5S,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl]-acetamide
  参考文献：
  名称：

  用于强效抗肿瘤抗生素帕他霉素的官能化环戊烷的合成

  摘要：

  通过 Overman 重排和 Pauson-Khand 环化作为关键步骤，从双丙酮-D-葡萄糖开始，构建了一种三环化合物，包括用于抗肿瘤抗生素帕他霉素的环戊烷结构。

  DOI：

  10.1055/s-2004-837223

文献信息

• One-Step Transformation of Trichloroacetamide into Isonitrile
  作者：Masaatsu Adachi、Tadachika Miyasaka、Honoka Hashimoto、Toshio Nishikawa

  DOI：10.1021/acs.orglett.6b03583

  日期：2017.1.20

  A one-step transformation of trichloroacetamide, a protective group for the amine function, into isonitrile was successfully developed. The substrate scope and functional group tolerance of this procedure are also described.

  成功开发出了一步法将三氯乙酰胺（一种具有胺功能的保护基团）转化为异腈。还描述了该过程的底物范围和官能团耐受性。
• Synthesis of Functionalized Cyclopentane for Pactamycin, a Potent Antitumor Antibiotic
  作者：Toshio Nishikawa、Minoru Isobe、Takashi Tsujimoto、Daisuke Urabe

  DOI：10.1055/s-2004-837223

  日期：——

  A tricyclic compound including a cyclopentane structure for pactamycin, an antitumor antibiotic, was constructed by Overman rearrangement and Pauson-Khand cyclization as key steps starting from diacetone-D-glucose.

  通过 Overman 重排和 Pauson-Khand 环化作为关键步骤，从双丙酮-D-葡萄糖开始，构建了一种三环化合物，包括用于抗肿瘤抗生素帕他霉素的环戊烷结构。
• One-Pot Transformation of Trichloroacetamide into Readily Deprotectable Carbamates
  作者：Toshio Nishikawa、Daisuke Urabe、Miho Tomita、Takashi Tsujimoto、Tomoko Iwabuchi、Minoru Isobe

  DOI：10.1021/ol061123c

  日期：2006.7.1

  A trichloroacetamide group was converted to an isocyanate, which was in situ captured by a variety of alcohols in the presence of CuCl and n-BuN4Cl to afford the corresponding carbamates. The scope and limitation of this transformation are also described.