(1R,2R,3S,4R,5R)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-propenyloxy-tetrahydro-furo[2,3-d][1,3]dioxole | 142435-25-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3S,4R,5R)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-propenyloxy-tetrahydro-furo[2,3-d][1,3]dioxole
• 英文别名: (3aR,5R,6S,6aR)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-6-[(Z)-prop-1-enoxy]-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 142435-25-4
• 化学式: C₁₅H₂₄O₆
• 分子量: 300.352
• InChiKey: RSCYQPRGEVQBEZ-PBTIICLBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  55.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,4R,5R)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-propenyloxy-tetrahydro-furo[2,3-d][1,3]dioxole 在 氧气 、 copper(l) chloride 、 palladium dichloride 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.33h， 以81%的产率得到双丙酮葡萄糖
  参考文献：
  名称：

  A study of catalysed Wacker reaction for the deprotection of prop-2-enyl and prop-1-enyl ethers

  摘要：

  Pd(II)Cl-2 (1 mole equivalent)/CuCl/DMF-H2O/O-2/2h catalysed oxidation of various prop-2-enyl ethers 1a-12a is reported to result in the formation of Wacker ketones 1b,3b,5b,6b,9b,11b,12b (12-51%), hydrolysis products 2c,4c-7c,9c-12c (12-43%) and eta(2)-vinyl complexes of palladium chloride 2d,4d,7d,8d (52-94%) respectively. The corresponding prop-1-enyl ethers 2e,4e-12e under similar conditions react with a catalytic amount of Pd(II)Cl-2 (0.2 mole equivalent) rapidly (15-20 min.) to give exclusively hydroxy compounds 2c,4c-12c respectively in good yields (75-97%). (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10198-3
• 作为产物：
  描述：

  (3R,4S)-3-[(4R)-2,2-二甲基-1,3-二氧戊环-4-基]-7,7-二甲基-4-丙-2-烯氧基-2,6,8-三氧杂双环[3.3.0]辛烷 在 potassium tert-butylate 作用下， 以 二甲基亚砜 为溶剂， 以62%的产率得到(1R,2R,3S,4R,5R)-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-6-propenyloxy-tetrahydro-furo[2,3-d][1,3]dioxole
  参考文献：
  名称：

  Carbohydrates as Chiral Auxiliaries. [2+2) Cycloadditions of Ketenes to Enol Ethers

  摘要：

  通过碳水化合物烯醇醚和取代酮之间的 [2+2] 环加成反应，合成了含有多达四个手性中心的对映体纯环丁醇。通过酸催化裂解与碳水化合物助剂的同分异构乙缩醛连接，得到了(1R,2R,3S)-3-苄氧基-2-甲基环丁醇，产量很高，而且所有生成的手性中心都保持不变。合成的环丁醇的绝对构型是通过单晶 X 射线分析确定的。

  DOI：

  10.1055/s-1994-25693

文献信息

• Efficient Allyl to Propenyl Isomerization in Functionally Diverse Compounds with a Thermally Modified Grubbs Second-Generation Catalyst
  作者：Stephen Hanessian、Simon Giroux、Andreas Larsson

  DOI：10.1021/ol062167o

  日期：2006.11.1

  Heating compounds containing C-allylic appendages in MeOH in the presence of 10 mol % of Grubbs second-generation catalyst at 0.075 M substrate concentration leads to the corresponding 2-propenyl derivatives without further conjugation in the cases of ketones, esters, and lactams. The reaction is applicable to a large variety of functionally relevant terminal olefins, including O- and N-allyl ethers

  在10摩尔％的Grubbs第二代催化剂存在下，在0.075 M底物浓度下，在MeOH中加热包含C-烯丙​​基附件的化合物，在酮，酯和内酰胺的情况下，无需进一步偶联即可得到相应的2-丙烯基衍生物。该反应适用于多种功能相关的末端烯烃，包括O-和N-烯丙基醚。[反应：请参见文字]。
• Carbohydrates as Chiral Auxiliaries. [2+2) Cycloadditions of Ketenes to Enol Ethers
  作者：Ingo Ganz、Horst Kunz

  DOI：10.1055/s-1994-25693

  日期：——

  Enantiomerically pure cyclobutanols containing up to four chiral centers were synthesized applying a [2+2] cycloaddition between carbohydrate enol ethers and substituted ketenes. Acid-catalysed cleavage of the anomeric acetal linkage to the carbohydrate auxiliary gave (1R,2R,3S)-3-benzyloxy-2-methylcyclobutanol in high yield and under conservation of all generated chiral centers. The absolute configuration of the synthesized cyclobutanols was determined by single-crystal X-ray analysis.

  通过碳水化合物烯醇醚和取代酮之间的 [2+2] 环加成反应，合成了含有多达四个手性中心的对映体纯环丁醇。通过酸催化裂解与碳水化合物助剂的同分异构乙缩醛连接，得到了(1R,2R,3S)-3-苄氧基-2-甲基环丁醇，产量很高，而且所有生成的手性中心都保持不变。合成的环丁醇的绝对构型是通过单晶 X 射线分析确定的。
• A study of catalysed Wacker reaction for the deprotection of prop-2-enyl and prop-1-enyl ethers
  作者：Hari Babu Mereyala、Sarita Reddy Lingannagaru

  DOI：10.1016/s0040-4020(97)10198-3

  日期：1997.12

  Pd(II)Cl-2 (1 mole equivalent)/CuCl/DMF-H2O/O-2/2h catalysed oxidation of various prop-2-enyl ethers 1a-12a is reported to result in the formation of Wacker ketones 1b,3b,5b,6b,9b,11b,12b (12-51%), hydrolysis products 2c,4c-7c,9c-12c (12-43%) and eta(2)-vinyl complexes of palladium chloride 2d,4d,7d,8d (52-94%) respectively. The corresponding prop-1-enyl ethers 2e,4e-12e under similar conditions react with a catalytic amount of Pd(II)Cl-2 (0.2 mole equivalent) rapidly (15-20 min.) to give exclusively hydroxy compounds 2c,4c-12c respectively in good yields (75-97%). (C) 1997 Elsevier Science Ltd.