6-oxo-4,6,7,8-tetrahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolane]-8a(3H)carbaldehyde

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-oxo-4,6,7,8-tetrahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolane]-8a(3H)carbaldehyde
• 英文别名: 7'-oxospiro[1,3-dioxolane-2,3'-2,4,5,6-tetrahydro-1H-naphthalene]-4'a-carbaldehyde
• 化学式: C₁₃H₁₆O₄
• 分子量: 236.268
• InChiKey: BMEAQPHEVDNBHD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  17
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  6-oxo-4,6,7,8-tetrahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolane]-8a(3H)carbaldehyde 在 titanium(IV) isopropylate 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 11.0h， 生成 tert-butyl ethyl((6-oxo-4,6,7,8-tetrahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolan]-8a(3H)-yl)methyl)carbamate
  参考文献：
  名称：

  Synthetic Studies on Acochlearine: Construction of the A/B/C/E/F Ring System

  摘要：

  Synthetic studies on acochlearine are described. The pentacyclic A/B/C/E/F ring system of acochlearine was constructed from a bicyclic enone via chemoselective reductive amination, one-pot bromination-intramolecular Mannich reaction cascade, and 6-electrocyclization.

  DOI：

  10.1055/s-0035-1560384
• 作为产物：
  描述：

  4a-carbomethoxy-4,4a,7,8-tetrahydronaphthalene-2,6(3H,5H)-dione 6-ethylene acetal 在 lithium aluminium tetrahydride 、 silica gel 、 sodium sulfate 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 13.0h， 生成 6-oxo-4,6,7,8-tetrahydro-1H-spiro[naphthalene-2,2'-[1,3]dioxolane]-8a(3H)carbaldehyde
  参考文献：
  名称：

  Synthetic Studies on Acochlearine: Construction of the A/B/C/E/F Ring System

  摘要：

  Synthetic studies on acochlearine are described. The pentacyclic A/B/C/E/F ring system of acochlearine was constructed from a bicyclic enone via chemoselective reductive amination, one-pot bromination-intramolecular Mannich reaction cascade, and 6-electrocyclization.

  DOI：

  10.1055/s-0035-1560384

文献信息

• Synthetic Studies on Acochlearine: Construction of the A/B/C/E/F Ring System
  作者：Hidetoshi Tokuyama、Kosuke Fujioka、Naoya Miyamoto、Hiroki Toya、Kentaro Okano

  DOI：10.1055/s-0035-1560384

  日期：——

  Synthetic studies on acochlearine are described. The pentacyclic A/B/C/E/F ring system of acochlearine was constructed from a bicyclic enone via chemoselective reductive amination, one-pot bromination-intramolecular Mannich reaction cascade, and 6-electrocyclization.