(4-bromo-3H-inden-1-yl)oxy-tri(propan-2-yl)silane | 1216934-77-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 茚和异茚
• 英文名称: (4-bromo-3H-inden-1-yl)oxy-tri(propan-2-yl)silane
• CAS: 1216934-77-8
• 化学式: C₁₈H₂₇BrOSi
• 分子量: 367.401
• InChiKey: YUFWVWKUNOODKA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.54
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (4-bromo-3H-inden-1-yl)oxy-tri(propan-2-yl)silane 在 lithium diisopropyl amide 、 copper dichloride 作用下， 以 四氢呋喃 、 正庚烷 、 乙基苯 为溶剂， 反应 0.17h， 生成 (3S)-4-bromo-3-[(1R)-7-bromo-3-oxo-1,2-dihydroinden-1-yl]-2,3-dihydroinden-1-one 、 (3S)-4-bromo-3-[(1S)-7-bromo-3-oxo-1,2-dihydroinden-1-yl]-2,3-dihydroinden-1-one
  参考文献：
  名称：

  Synthesis of a Basket-Shaped C₅₆H₃₈ Hydrocarbon as a Precursor toward an End-Cap Template for Carbon [6,6]Nanotubes

  摘要：

  A basket-shaped C56H38 hydrocarbon (3) possessing a 30-carbon difluorenonaphthacenyl core that can be mapped onto the surface of C-78 was synthesized from 4-bromo-1-indanone. The first stage of the synthesis involved the preparation of tetraketone 10 as a key intermediate. The use of cascade cyclization reactions of benzannulated enyne-allenes as key features in the next stage of the synthetic sequence provides an efficient route to 3 from 4-bromo-1-indanone in 12 steps. The all-cis relationship among the methyl groups and the methine hydrogens causes the two benzofluorenyl units in 3 to be in an essentially perpendicular orientation to each other. Hydrocarbon 3 and its derivatives could serve as attractive precursors leading to a geodesic C68H26 end-cap template for carbon [6,6]nanotubes.

  DOI：

  10.1021/jo100132v
• 作为产物：
  描述：

  4-溴-1-茚酮 、 三异丙基硅基三氟甲磺酸酯 在 三乙胺 作用下， 以 氯仿 为溶剂， 生成 (4-bromo-3H-inden-1-yl)oxy-tri(propan-2-yl)silane
  参考文献：
  名称：

  1-茚满酮环扩成 2-卤代-1-萘酚作为 Gilvocarcin 天然产品的切入点

  摘要：

  在此，我们描述了 1-茚满酮的两步环扩展以提供 2-氯/溴-1-萘酚（32 个例子）。所开发的方法显示出广泛的官能团耐受性，受益于温和的反应条件，并且能够快速获得吉沃卡星天然产物的四环核心。正交功能化的产品允许选择性后修饰，如 defucogilvocarcin M 的全合成所示。为了选择性氧化色烯，开发了温和的区域选择性氧化方案（DDQ 和 TBHP）。

  DOI：

  10.1021/acs.orglett.1c03530

文献信息

• Ring Expansion of 1-Indanones to 2-Halo-1-naphthols as an Entry Point to Gilvocarcin Natural Products
  作者：Ivica Zamarija、Benjamin J. Marsh、Thomas Magauer

  DOI：10.1021/acs.orglett.1c03530

  日期：2021.12.3

  functional group tolerance, benefits from mild reaction conditions, and enables rapid access to the tetracyclic core of gilvocarcin natural products. The orthogonally functionalized products allow for selective postmodifications as exemplified in the total synthesis of defucogilvocarcin M. For the selective oxidation of the chromene, a mild and regioselective oxidation protocol (DDQ and TBHP) was developed

  在此，我们描述了 1-茚满酮的两步环扩展以提供 2-氯/溴-1-萘酚（32 个例子）。所开发的方法显示出广泛的官能团耐受性，受益于温和的反应条件，并且能够快速获得吉沃卡星天然产物的四环核心。正交功能化的产品允许选择性后修饰，如 defucogilvocarcin M 的全合成所示。为了选择性氧化色烯，开发了温和的区域选择性氧化方案（DDQ 和 TBHP）。
• Synthesis of a Basket-Shaped C₅₆H₃₈ Hydrocarbon as a Precursor toward an End-Cap Template for Carbon [6,6]Nanotubes
  作者：Hu Cui、Novruz G. Akhmedov、Jeffrey L. Petersen、Kung K. Wang

  DOI：10.1021/jo100132v

  日期：2010.3.19

  A basket-shaped C56H38 hydrocarbon (3) possessing a 30-carbon difluorenonaphthacenyl core that can be mapped onto the surface of C-78 was synthesized from 4-bromo-1-indanone. The first stage of the synthesis involved the preparation of tetraketone 10 as a key intermediate. The use of cascade cyclization reactions of benzannulated enyne-allenes as key features in the next stage of the synthetic sequence provides an efficient route to 3 from 4-bromo-1-indanone in 12 steps. The all-cis relationship among the methyl groups and the methine hydrogens causes the two benzofluorenyl units in 3 to be in an essentially perpendicular orientation to each other. Hydrocarbon 3 and its derivatives could serve as attractive precursors leading to a geodesic C68H26 end-cap template for carbon [6,6]nanotubes.