3,3-二甲基-4,4-(亚乙二氧基)-1-丁醇 | 100366-95-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧戊环
• 中文名称: 3,3-二甲基-4,4-(亚乙二氧基)-1-丁醇
• 英文名称: 3,3-dimethyl-4,4-(ethylenedioxy)-1-butanol
• 英文别名: 4,4-Ethylenedioxy-3,3-dimethylbutan-1-ol；3-(1,3-dioxolan-2-yl)-3-methylbutan-1-ol；3-(1,3-Dioxolan-2-yl)-3-methylbutan-1-ol
• CAS: 100366-95-8
• 化学式: C₈H₁₆O₃
• 分子量: 160.213
• InChiKey: RPJKXAPATCDGJJ-UHFFFAOYSA-N

物化性质

• 沸点：
  228.4±15.0 °C(Predicted)
• 密度：
  1.060±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  1.0
• 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：

  3,3-二甲基-4,4-(亚乙二氧基)-1-丁醇 在 sodium acetate 、 pyridinium chlorochromate 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 以87%的产率得到3,3-dimethyl-4,4-(ethylenedioxy)-1-butanal
  参考文献：
  名称：

  Synthesis of .DELTA.3-1-methylene-1-carbacephems

  摘要：

  The total synthesis of (+/-)-1-methylene-2,2- dimethyl-7-amino-1-carbacephem-4-carboxylic acid (1) is described. The reaction scheme was essentially that described by Christensen et al. for the synthesis of (+/-)-1-carbacephems. In vitro antibacterial activities of the 7-phenoxyacetyl and 7-D-alpha-phenylglycyl derivatives of 1 were compared with those of 7-(phenoxyacetamido)desacetoxycephalosporanic acid and cefalexin. Derivatives of 1 were 2-4 times less active against most of the sensitive organisms than the corresponding 7-aminodesacetoxycephalosporanic acid analogues. The activity of the 7-D-alpha-phenylglycyl derivative of 1 however was about 20 times lower than that of cefalexin when measured against Staphylococcus aureus ATCC 6538P.

  DOI：

  10.1021/jm00155a013
• 作为产物：
  描述：

  3,3-dimethyl-4,4-(ethylenedioxy)-1-butanal 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 生成 3,3-二甲基-4,4-(亚乙二氧基)-1-丁醇
  参考文献：
  名称：

  Facile construction of the bicyclo[6.4.0]dodecane system by the intramolecular Michael addition of sulfonyl carbanion

  摘要：

  通过磺酰基碳酰离子的分子内迈克尔加成，合成了双环[6.4.0]十二烷体系。

  DOI：

  10.1039/cc9960001801

文献信息

• Generation of Dithianyl and Dioxolanyl Radicals Using Photoredox Catalysis: Application in the Total Synthesis of the Danshenspiroketallactones via Radical Relay Chemistry
  作者：Yifan Deng、Minh D. Nguyen、Yike Zou、K. N. Houk、Amos B. Smith

  DOI：10.1021/acs.orglett.9b00271

  日期：2019.3.15

  Visible-light-induced generation of dithianyl and dioxolanyl radicals via selective hydrogen atom transfer (HAT) has been achieved. This radical relay tactic enables remote C(sp3)–H functionalization to permit rapid access to polyol and spiroketal segments, and in turn has been exploited as a key synthetic construct in the total synthesis of the danshenspiroketallactones. The conformational stability

  已经实现了通过选择性氢原子转移（HAT）的可见光诱导的二噻吩基和二氧戊环基自由基的产生。这种基本的中继策略使远程C（sp 3）-H功能化成为可能，从而允许快速访问多元醇和螺环酮链段，从而又被用作丹参螺酮内酯全合成中的关键合成结构。还通过实验和DFT计算确定了丹参螺酮内酯的构象稳定性。
• Hexamethyldisilazanes mediated one-pot intramolecular Michael addition–olefination reactions leading to exo-olefinated bicyclo[6.4.0]dodecanes
  作者：Hiroshi Fujishima、Hiroshi Takeshita、Shuichi Suzuki、Masahiro Toyota、Masataka Ihara

  DOI：10.1039/a904484a

  日期：——

  A novel one-pot reaction for the synthesis of exo-olefinated bicyclo[6.4.0]dodecanes 23 has been developed on the basis of an intramolecular Michael reaction of phenylsulfonyl compounds 4 with potassium hexamethyldisilazide (KHMDS) and a sequential reaction with an excess of methoxymethyl chloride (MOMCl). By this reaction, an exo-olefin group was regioselectively introduced at the α-position to the carbonyl group in the 6-membered ring in high yield. The regioselective introduction of the olefin moiety could be envisaged to proceed through a Mannich-type reaction involving the aminomethylating agent 24, which, in turn, is generated in situ by the action of HMDS on MOMCl.

  开发了一种新颖的一锅法反应，用于合成外烯基双环[6.4.0]十二烷 23，该反应基于苯基磺酰化合物 4 与六甲基二硅氮化钾（KHMDS）进行的分子内迈克尔反应，以及与过量的甲氧基甲基氯（MOMCl）进行的序贯反应。通过该反应，外烯基团以区域选择性的方式引入到6元环中的羰基α位，并获得了高产率。烯烃官能团的区域选择性引入可以设想是通过一种曼尼希反应进行的，该反应涉及氨基甲基化试剂24，该试剂又是在HMDS与MOMCl作用下就地生成的。
• Synthesis of .DELTA.3-1-methylene-1-carbacephems
  作者：Piet Herdewijn、Paul J. Claes、Hubert Vanderhaeghe

  DOI：10.1021/jm00155a013

  日期：1986.5

  The total synthesis of (+/-)-1-methylene-2,2- dimethyl-7-amino-1-carbacephem-4-carboxylic acid (1) is described. The reaction scheme was essentially that described by Christensen et al. for the synthesis of (+/-)-1-carbacephems. In vitro antibacterial activities of the 7-phenoxyacetyl and 7-D-alpha-phenylglycyl derivatives of 1 were compared with those of 7-(phenoxyacetamido)desacetoxycephalosporanic acid and cefalexin. Derivatives of 1 were 2-4 times less active against most of the sensitive organisms than the corresponding 7-aminodesacetoxycephalosporanic acid analogues. The activity of the 7-D-alpha-phenylglycyl derivative of 1 however was about 20 times lower than that of cefalexin when measured against Staphylococcus aureus ATCC 6538P.
• Facile construction of the bicyclo[6.4.0]dodecane system by the intramolecular Michael addition of sulfonyl carbanion
  作者：Masataka Ihara、Shuichi Suzuki、Yuji Tokunaga、Hiroshi Takeshita、Keiichiro Fukumoto

  DOI：10.1039/cc9960001801

  日期：——

  A bicyclo[6.4.0]dodecane system is synthesised via the intramolecular Michael addition of sulfonyl carbanion.

  通过磺酰基碳酰离子的分子内迈克尔加成，合成了双环[6.4.0]十二烷体系。