(R)-2-methyl-1,4-dioxaspiro<4.5>decane-2-methanol | 133868-50-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (R)-2-methyl-1,4-dioxaspiro<4.5>decane-2-methanol
• 英文别名: 1-propanol-(2S),3-diol cyclohexyl ketal；[(3R)-3-methyl-1,4-dioxaspiro[4.5]decan-3-yl]methanol
• CAS: 133868-50-5
• 化学式: C₁₀H₁₈O₃
• 分子量: 186.251
• InChiKey: WCZLLEBNALONQV-SECBINFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (R)-2-methyl-1,4-dioxaspiro<4.5>decane-2-methanol 在 重铬酸吡啶 、 草酰氯 、 potassium tert-butylate 、 4-甲基苯磺酸吡啶 、 sodium hydride 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 37.0h， 生成 (1R,3aR,7aR)-7a-Methyl-1-[(R)-1-methyl-4-((R)-2-methyl-1,4-dioxa-spiro[4.5]dec-2-yl)-but-3-ynyl]-octahydro-inden-4-one
  参考文献：
  名称：

  Synthesis and biological evaluation of 1α-hydroxy-25(R and S)-25,26-Epoxy-23-yne vitamin D3 and of 1α,25(R and S),26-Trihydroxy-23-yne vitamin D3

  摘要：

  The synthesis of both 1 alpha-hydroxy-25(R and S)-25,26-epoxy-23-yne vitamin D-3 and of both 1 alpha,2S(R and S),26-trihydroxy-23-yne vitamin D-3 is described. Biological evaluation includes the study of calcemic effect, receptor binding and cell differentiation. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00138-8
• 作为产物：
  描述：

  (S)-2-Methyl-1,4-dioxa-spiro[4.5]decane-2-carboxylic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester 在 二异丁基氢化铝 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 生成 (R)-2-methyl-1,4-dioxaspiro<4.5>decane-2-methanol
  参考文献：
  名称：

  Synthesis and biological evaluation of 1α-hydroxy-25(R and S)-25,26-Epoxy-23-yne vitamin D3 and of 1α,25(R and S),26-Trihydroxy-23-yne vitamin D3

  摘要：

  The synthesis of both 1 alpha-hydroxy-25(R and S)-25,26-epoxy-23-yne vitamin D-3 and of both 1 alpha,2S(R and S),26-trihydroxy-23-yne vitamin D-3 is described. Biological evaluation includes the study of calcemic effect, receptor binding and cell differentiation. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0960-894x(97)00138-8

文献信息

• Studies on the Stereoselective Synthesis of the Marine Antitumor Agent Eleutherobin
  作者：Rich Carter、Kevin Hodgetts、Jeff McKenna、Philip Magnus、Stephen Wren

  DOI：10.1016/s0040-4020(00)00309-4

  日期：2000.6

  14 to the aldehyde 21, followed by oxidation, dissolving metal reduction and stereoselective reduction of the C8 carbonyl group resulted in 29, which has the correct stereochemistry at C8 and C9. Further conversion of 29 into 37, and attempted intramolecular cyclization resulted in fragmentation to the furan 39 and 38. Asymmetric epoxidation of the allylic alcohols 42 and 48 resulted in neighboring

  （+） -香芹酮已被转换成砜14，其包括细胞毒性的倍半萜的左手侧，eleutherobin 1。朱莉娅将14与醛21偶联，然后进行氧化，溶解金属并将其立体选择性还原为C8羰基，得到29，该化合物在C8和C9处具有正确的立体化学。29进一步转化为37，并尝试进行分子内环化，导致呋喃39和38断裂。烯丙醇42和48的不对称环氧化导致从相邻的二甲氧基乙缩醛和形成重排的氧杂环庚烷衍生物的邻基参与44，45和49分别。
• Facile chemoenzymic preparation of enantiomerically pure 2-methylglycerol derivatives as versatile trifunctional C4-synthons
  作者：Beat Wirz、Richard Barner、Joseph Huebscher

  DOI：10.1021/jo00067a034

  日期：1993.7

  Both enantiomers of a series of synthetically valuable 2-methylglycerol derivatives have been prepared with >99% ee using a chemoenzymatic reaction sequence. The introduction of chirality was achieved by enantioselective esterification of 1,2-O-protected 2-methylglycerol 3 or enantioselective hydrolysis of its butyryl ester 4. The enzymatic reaction proceeded with unusually high selectivity and velocity for a primary alcohol (ester) substrate.
• Herstellung von Dioxolanderivaten
  申请人：F. HOFFMANN-LA ROCHE AG

  公开号：EP0388778B1

  公开（公告）日：1996-01-10
• US5232852A
  申请人：——

  公开号：US5232852A

  公开（公告）日：1993-08-03
• US5283346A
  申请人：——

  公开号：US5283346A

  公开（公告）日：1994-02-01