5,6-dimethoxy-1-(toluene-4-sulfonyl)-9-(triisopropylsilanyloxy)-2,3-dihydro-1H-azacyclohepta[a]acenaphthylene | 473840-73-2

• 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: 5,6-dimethoxy-1-(toluene-4-sulfonyl)-9-(triisopropylsilanyloxy)-2,3-dihydro-1H-azacyclohepta[a]acenaphthylene
• 英文别名: [15,16-Dimethoxy-10-(4-methylphenyl)sulfonyl-10-azatetracyclo[7.7.1.02,8.013,17]heptadeca-1,3,5,7,9(17),13,15-heptaen-5-yl]oxy-tri(propan-2-yl)silane
• CAS: 473840-73-2
• 化学式: C₃₄H₄₃NO₅SSi
• 分子量: 605.871
• InChiKey: DLWUISMPWNKHBS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.58
• 重原子数：
  42
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  73.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,6-dimethoxy-1-(toluene-4-sulfonyl)-9-(triisopropylsilanyloxy)-2,3-dihydro-1H-azacyclohepta[a]acenaphthylene 在 aluminum oxide 、 potassium fluoride 作用下， 以 四氢呋喃 为溶剂， 反应 72.0h， 以57%的产率得到pareitropone
  参考文献：
  名称：

  Total Synthesis of the Tropoloisoquinoline Alkaloid Pareitropone via Alkynyliodonium Salt Chemistry and Related Studies

  摘要：

  The first chemical synthesis of pareitropone, by a route featuring application of alkynyliodonium salt chemistry, is described. The key transform initiates with addition of an alkylidenecarbene, derived by intramolecular nucleophile addition to the alkynyliodonium moiety, to a proximal aromatic ring. This addition delivers a highly strained norcaradiene substructure that rapidly reorganizes to furnish the pareitropone skeleton.

  DOI：

  10.1021/jo026337w
• 作为产物：
  描述：

  N-{2-[5,6-dimethoxy-2-(tributylstannylethynyl)-4'-(triisopropylsilanyloxy)biphenyl-3-yl]ethyl}-4-methylbenzenesulfonamide 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 二氯甲烷 为溶剂， 反应 1.75h， 生成 5,6-dimethoxy-1-(toluene-4-sulfonyl)-9-(triisopropylsilanyloxy)-2,3-dihydro-1H-azacyclohepta[a]acenaphthylene
  参考文献：
  名称：

  Total Synthesis of the Tropoloisoquinoline Alkaloid Pareitropone via Alkynyliodonium Salt Chemistry and Related Studies

  摘要：

  The first chemical synthesis of pareitropone, by a route featuring application of alkynyliodonium salt chemistry, is described. The key transform initiates with addition of an alkylidenecarbene, derived by intramolecular nucleophile addition to the alkynyliodonium moiety, to a proximal aromatic ring. This addition delivers a highly strained norcaradiene substructure that rapidly reorganizes to furnish the pareitropone skeleton.

  DOI：

  10.1021/jo026337w

文献信息

• Total Synthesis of the Tropoloisoquinoline Alkaloid Pareitropone via Alkynyliodonium Salt Chemistry and Related Studies
  作者：Ken S. Feldman、Timothy D. Cutarelli、Romina Di Florio

  DOI：10.1021/jo026337w

  日期：2002.11.1

  The first chemical synthesis of pareitropone, by a route featuring application of alkynyliodonium salt chemistry, is described. The key transform initiates with addition of an alkylidenecarbene, derived by intramolecular nucleophile addition to the alkynyliodonium moiety, to a proximal aromatic ring. This addition delivers a highly strained norcaradiene substructure that rapidly reorganizes to furnish the pareitropone skeleton.
• Alkynyliodonium Salts in Organic Synthesis. Application to the Total Synthesis of the Tropoloisoquinoline Alkaloid Pareitropone
  作者：Ken S. Feldman、Timothy D. Cutarelli

  DOI：10.1021/ja0277430

  日期：2002.10.1

  The synthesis of the tropoloisoquinoline alkaloid pareitropone has been accomplished in 14 steps from 2,3,4-trimethoxybenzoic acid. The key transformations include the generation of an alkylidenecarbene intermediate through intramolecular addition of a tosylamide anion to an alkynyliodonium salt, and the cycloaddition of that carbene to a peri positioned aromatic ring to afford a cycloheptatrienylidene product featuring the intact pareitropone skeleton.