(1S,3R,4R,6S,8R,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-2,5,11-trioxabicyclo[6.3.0]undecane | 848821-20-5

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: (1S,3R,4R,6S,8R,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-2,5,11-trioxabicyclo[6.3.0]undecane
• 英文别名: (2R,3R,5S,6aR,8R,9aS)-5,8-bis(iodomethyl)-2,3-diphenyl-2,3,5,6,6a,7,8,9a-octahydrofuro[2,3-e][1,4]dioxocine
• CAS: 848821-20-5
• 化学式: C₂₂H₂₄I₂O₃
• 分子量: 590.24
• InChiKey: BCRHHVJYWPQBFX-DRGMGAIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  27
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (1S,3R,4R,6S,8R,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-2,5,11-trioxabicyclo[6.3.0]undecane 在 sodium chlorite 、 sodium dihydrogenphosphate 、 copper(l) iodide 、 2-甲基-2-丁烯 、 ammonium cerium(IV) nitrate 、 水 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 乙醚 、 水 、 乙腈 、 叔丁醇 为溶剂， 反应 7.5h， 生成 (3R,5R,2'R)-3-(2-hydroxydodec-11-enyl)-5-iodomethyldihydrofuran-2-one
  参考文献：
  名称：

  σ对称二烯乙缩醛的双重碘醚化，可在一次操作中安装四个立体异构中心：短时不对称的总合成红花烯内酯。

  摘要：

  DOI：

  10.1002/anie.200461584
• 作为产物：
  描述：

  氢胺 在 N-碘代丁二酰亚胺 、 甲氧基三甲基硅烷 、 三氟甲磺酸三甲基硅酯 、 水 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 27.0h， 生成 (1S,3R,4R,6S,8R,10R)-6,10-bis(iodomethyl)-3,4-diphenyl-2,5,11-trioxabicyclo[6.3.0]undecane
  参考文献：
  名称：

  σ对称二烯乙缩醛的双重碘醚化，可在一次操作中安装四个立体异构中心：短时不对称的总合成红花烯内酯。

  摘要：

  DOI：

  10.1002/anie.200461584

文献信息

• Facile formation of tetrahydrofurans with multiple chiral centers using double iodoetherification of σ-symmetric diene acetals: short asymmetric total synthesis of rubrenolide and rubrynolide
  作者：Hiromichi Fujioka、Yusuke Ohba、Hideki Hirose、Kenji Nakahara、Kenichi Murai、Yasuyuki Kita

  DOI：10.1016/j.tet.2008.02.088

  日期：2008.5

  novel double intramolecular iodoetherification of σ-symmetric diene acetals from (R,R)-hydrobenzoin occurred in highly diastereoselective manners to give tetrahydrofuran moieties with multiple chiral centers in a one-pot operation. The chemoselective discrimination of the two iodomethyl functions in the products was attained in various reactions. The reaction was applied to the concise asymmetric syntheses

  从（R，R）-氢安息香素中σ对称二烯乙缩醛的新型双分子碘代醚化反应以高度非对映选择性的方式进行，以一锅操作得到具有多个手性中心的四氢呋喃部分。在各种反应中实现了产物中两个碘甲基官能团的化学选择性鉴别。该反应被用于简单的不对称合成的红花烯内酯和红花内酯，其中手性助剂的单元作为模板来实现化学选择性和作为羟基官能团的保护基。
• Mild and Efficient Removal of Hydroxyethyl Unit from 2-Hydroxyethyl Ether Derivatives Leading to Alcohols
  作者：Hiromichi Fujioka、Yusuke Ohba、Hideki Hirose、Kenichi Murai、Yasuyuki Kita

  DOI：10.1021/ol051135i

  日期：2005.7.1

  CAN is a good reagent for the transformation of 2-hydroxyethyl ether units to alcohols. Significantly, many functional groups can tolerate the reaction conditions, although they do not survive under many previously reported removal conditions. The reaction mechanism is clarified.
• Cerium ammonium nitrate (CAN) for mild and efficient reagent to remove hydroxyethyl units from 2-hydroxyethyl ethers and 2-hydroxyethyl amines
  作者：Hiromichi Fujioka、Hideki Hirose、Yusuke Ohba、Kenichi Murai、Kenji Nakahara、Yasuyuki Kita

  DOI：10.1016/j.tet.2006.11.004

  日期：2007.1

  Cerium ammonium nitrate (CAN) removed hydroxyethyl units from 2-hydroxyethyl ethers and 2-hydroxyethyl amines to produce alcohols and amines in good yields. Especially, removal of the 2-hydroxyethyl ethers from C-2-symmetric diols, chiral 2,3-butanediol and chiral hydrobenzoin, was very useful for asymmetric syntheses using C-2-symmetric diols. The reactions using dual abilities of CAN, i.e., the ability for removal of the 2-hydroxyethyl unit and the ability for acetal hydrolysis by a single electron transfer, were also achieved Successfully. The reaction conditions were very mild and efficient, and many functional groups, which can be affected under normal conditions, were unaffected during the reaction. (c) 2006 Published by Elsevier Ltd.