(1'R,2'S,6'R,7'R)-spiro[1,3-dioxolane-2,8'-4-oxatricyclo[5.2.1.02,6]decane]-3',5'-dione | 133738-95-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1'R,2'S,6'R,7'R)-spiro[1,3-dioxolane-2,8'-4-oxatricyclo[5.2.1.02,6]decane]-3',5'-dione
• CAS: 133738-95-1；133813-34-0
• 化学式: C₁₁H₁₂O₅
• 分子量: 224.213
• InChiKey: WWWJYBBPKRXBRV-OOJXKGFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  马来酸酐 、 2-环戊烯-1-酮缩乙醛 以 乙腈 为溶剂， 反应 2.0h， 生成 (1'R,2'R,6'S,7'R)-spiro[1,3-dioxolane-2,8'-4-oxatricyclo[5.2.1.02,6]decane]-3',5'-dione 、 (1'R,2'S,6'R,7'R)-spiro[1,3-dioxolane-2,8'-4-oxatricyclo[5.2.1.02,6]decane]-3',5'-dione
  参考文献：
  名称：

  Reaction of cyclopent-2-en-1-one ethylene acetal with dienophiles via its ring-opened enol ether form. Single step synthesis of norbornan-2-one ethylene acetals

  摘要：

  环戊烯-2-酮乙烯缩醛在中性条件下通过其开环的烯醇醚2-(2-羟基乙氧基)环戊-1,3-二烯与多种二烯亲体发生Diels–Alder反应，生成诺博烷-2-酮乙烯缩醛。

  DOI：

  10.1039/c39910000037

文献信息

• Reaction of cyclopent-2-en-1-one ethylene acetal with dienophiles via its ring-opened enol ether form. Single step synthesis of norbornan-2-one ethylene acetals
  作者：Masakazu Ohkita、Takashi Tsuji、Shinya Nishida

  DOI：10.1039/c39910000037

  日期：——

  Cyclopent-2-en-1-one ethylene acetal undergoes Diels–Alder reaction with a variety of dienophiles via its ring-opened enol ether, 2-(2-hydroxyethoxy)cyclopenta-1,3-diene, under neutral conditions to give norbornan-2-one ethylene acetals.

  环戊烯-2-酮乙烯缩醛在中性条件下通过其开环的烯醇醚2-(2-羟基乙氧基)环戊-1,3-二烯与多种二烯亲体发生Diels–Alder反应，生成诺博烷-2-酮乙烯缩醛。
• A one-step synthesis of 2-norbornanone ethylene acetals from 2-cyclopenten-1-one ethylene acetals and dienophiles via [2 + 4] cycloaddition of in situ generated 2-(2-hydroxyethoxy)cyclopenta-1,3-dienes and intramolecular reacetalization
  作者：Masakazu Ohkita、Osamu Nishizawa、Takashi Tsuji、Shinya Nishida

  DOI：10.1021/jo00071a033

  日期：1993.9

  2-(2-Hydroxyethoxy)cyclopenta-1,3-diene (5) which is generated reversibly from 2-cyclopenten-1-one ethylene acetal (1) under mild, neutral conditions can be intercepted with a variety of dienophiles ultimately to give 2-norbornanone ethylene acetals in 62-100% yields. The addition reactions are highly stereo- and regioselective. Of the several solvents examined, acetonitrile is the most satisfactory. In CHCl3 or CCl4, decomposition of 1 is induced, leading to diminished yields of the adducts. The intermediate 5 is detected by UV spectroscopy, and its content relative to 1 at a stationary state at 70-degrees-C in acetonitrile is estimated to be ca. 0.2%. The reactions of the 2-, 3-, and 5-methyl-substituted derivatives 2-4 with dienophiles similarly led to the production of the corresponding 2-norbornanone acetals through the additions of the dienophiles to the 1,3-cyclopentadien-2-yl ether intermediates 6-8 selectively derived from 2-4 via 1,2-elimination. The formation of isomeric adducts resulting either from 1,4-elimination in 1-4 or from [1,51 hydrogen migration in the enol ether intermediates is not detected. The addition of 2-chloroacrylonitrile, a ketene equivalent, to 1-4 followed by alkaline hydrolysis provides singly acetalized 2,5-norbornadiones in two steps in good yields. 2-Cyclohexen-1-one ethylene acetal (44) also undergoes the addition of dienophiles in the [2 + 4] manner directly to give bicyclo[2.2.2]octan-2-one ethylene acetals, but is substantially less reactive than 1 toward this type of reaction.