1-methoxy-2-methoxycarbonyl-3-methyl-1-trimethylsiloxy-1,3-butadiene | 913977-88-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 1-methoxy-2-methoxycarbonyl-3-methyl-1-trimethylsiloxy-1,3-butadiene
• 英文别名: methyl 2-[methoxy(trimethylsilyloxy)methylidene]-3-methylbut-3-enoate
• CAS: 913977-88-5
• 化学式: C₁₁H₂₀O₄Si
• 分子量: 244.363
• InChiKey: IPVBTSOYECGSFF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  16.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-methoxy-2-methoxycarbonyl-3-methyl-1-trimethylsiloxy-1,3-butadiene 在 air 、 三乙酰氧基硼 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 methyl 1,8-dihydroxy-3-methylanthraquinone-2-carboxylate
  参考文献：
  名称：

  Concise Synthesis of (±)-γ-Indomycinone

  摘要：

  (±)-γ-吲哚霉素酮 (2) 的首次全合成以胡桃醌 (5) 为起始点，分九个步骤完成，包括 5 和二烯 6 的 Diels-Alder 反应以及炔酮 3 的正式 6-endo-dig 环化作为关键步骤。

  DOI：

  10.1246/cl.2006.1016
• 作为产物：
  描述：

  3,3-二甲基丙烯酸甲酯 在 六甲基磷酰三胺 、 sodium hydride 、 lithium diisopropyl amide 作用下， 反应 20.83h， 生成 1-methoxy-2-methoxycarbonyl-3-methyl-1-trimethylsiloxy-1,3-butadiene
  参考文献：
  名称：

  An integrated approach to the synthesis of contiguously substituted xanthopurpurins, pachybasins and purpurins.

  摘要：

  Alkylation, hydroxyalkylation and acylation of 3-methyl-, 3-methoxy- and 3,4-dimethoxycrotonates can be induced to occur exclusively in the alpha-Position. Conversion of the products to dienes then provides, through cycloaddition, a wide variety of substitution patterns. This approach is illustrated by simplified syntheses of a number of naturally occurring quinones and confirms the structures proposed for vismiaquinone C, 7-geranylemodin, cinnalutein, 4,5-dihydroxydigitolutein, 2-hydroxyislandicin 1-methyl ether and calyculatone 1-methyl ether.

  DOI：

  10.1016/s0040-4020(01)80322-7

文献信息

• Total Synthesis and Determination of the Absolute Configuration of Parimycin
  作者：Day-Shin Hsu、Jiun-Yi Huang

  DOI：10.1021/acs.orglett.9b02999

  日期：2019.9.20

  synthetic steps. Intermolecular Diels–Alder reaction of 6 with diene 7, cyclodehydrogenation catalyzed by iodine-dimethyl sulfoxide, and sodium dithionite reduction were the key steps. The absolute configuration of natural parimycin was determined to be S.

  （±）-parimycin和（R）-parimycin的第一批总合成是从O- methylnaphthazarin（6）分九个合成步骤完成的。关键的步骤是分子间Diels–Alder反应6与二烯7，碘-二甲基亚砜催化的环脱氢反应和连二亚硫酸钠还原。测定自然parimycin的绝对构型是小号。
• An integrated approach to the synthesis of contiguously substituted xanthopurpurins, pachybasins and purpurins.
  作者：Brigitte Caron、Paul Brassard

  DOI：10.1016/s0040-4020(01)80322-7

  日期：1993.1

  Alkylation, hydroxyalkylation and acylation of 3-methyl-, 3-methoxy- and 3,4-dimethoxycrotonates can be induced to occur exclusively in the alpha-Position. Conversion of the products to dienes then provides, through cycloaddition, a wide variety of substitution patterns. This approach is illustrated by simplified syntheses of a number of naturally occurring quinones and confirms the structures proposed for vismiaquinone C, 7-geranylemodin, cinnalutein, 4,5-dihydroxydigitolutein, 2-hydroxyislandicin 1-methyl ether and calyculatone 1-methyl ether.
• Concise Synthesis of (±)-γ-Indomycinone
  作者：Day-Shin Hsu、Takashi Matsumoto、Keisuke Suzuki

  DOI：10.1246/cl.2006.1016

  日期：2006.9

  The first total synthesis of (±)-γ-indomycinone (2) has been accomplished starting from juglone (5) in nine steps, including Diels–Alder reaction of 5 and diene 6 and the formal 6-endo-dig cyclization of alkynone 3 as the key steps.

  (±)-γ-吲哚霉素酮 (2) 的首次全合成以胡桃醌 (5) 为起始点，分九个步骤完成，包括 5 和二烯 6 的 Diels-Alder 反应以及炔酮 3 的正式 6-endo-dig 环化作为关键步骤。