(3-Iodo-1-methylpropoxy)trimethylsilane | 80900-43-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (3-Iodo-1-methylpropoxy)trimethylsilane
• 英文别名: 1-iodo-3-trimethylsilyloxybutane；1-iodo-3-trimethylsiloxybutane；4-Iodobutan-2-yloxy(trimethyl)silane
• CAS: 80900-43-2
• 化学式: C₇H₁₇IOSi
• 分子量: 272.201
• InChiKey: UBZXPNFKQLLLHU-UHFFFAOYSA-N

物化性质

• 沸点：
  198.1±23.0 °C(Predicted)
• 密度：
  1.325±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.05
• 重原子数：
  10
• 可旋转键数：
  4
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  9.2
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (3-Iodo-1-methylpropoxy)trimethylsilane 在 lithium aluminium tetrahydride 作用下， 以 乙醚 为溶剂， 反应 0.25h， 生成 1-hydroxymethyl-2,6-dimethoxy-1-(3'-trimethylsiloxybutyl)-2,5-cyclohexadiene
  参考文献：
  名称：

  甲氧基苯甲酸和酯的还原烷基化的改进方法：在合成双环酮中的应用

  摘要：

  通过金属氨溶液还原一系列甲氧基苯甲酸和酯，然后将得到的1,4-二氢产物原位烷基化或分离并随后烷基化。三种不同类型的烷基碘被用来引入丁酮或戊酮侧链的元素，作为添加稠合六元环的前奏，从而完成了Wieland-Miescher酮4a的几种类似物的制备，其中角取代基被充氧了。

  DOI：

  10.1016/s0040-4020(01)90577-0
• 作为产物：
  描述：

  2-甲基氧杂环丁烷 、 碘代三甲硅烷 以 氯仿 为溶剂， 反应 1.0h， 生成 (3-Iodo-1-methylpropoxy)trimethylsilane
  参考文献：
  名称：

  Spiroacetals and Other Venom Constituents as Potential Wasp Attractants

  摘要：

  The major volatile spiroacetals from the venom of both the common wasp, Vespula vulgaris and the German wasp V. germanica, viz. 7-methyl-1,6-dioxaspiro[4,5]decane and 7-ethyl-2-methyl-1,6-dioxaspiro[4,5]decane, respectively, were synthesized by known methods. These acetals, along with N-isopentylacetamide (the major volatile amide from wasp venom), 2-heptanone (a honeybee pheromone), 2-methyl-3-buten-2-ol (a component of hornet venom), cuticle wax from V. vulgaris, and venom sacs from both wasp species were assayed by EAG and olfactory bioassay for attractancy to V. vulgaris workers. Antennal responses to all test chemicals were recorded. Acetal isomers (+/-)-2 and (+/-)-3, N-isopentylacetamide, and 2-heptanone were attractive to V. vulgaris workers at levels of <1 mu mol. Greater quantities of the same compounds were repellent to V. vulgaris workers.

  DOI：

  10.1023/b:joec.0000006396.55680.b6

文献信息

• Synthesis of Spiroacetal Pheromones via Metalated Hydrazones
  作者：Dieter Enders、Walter Dahmen、Eleonore Dederichs、Winfried Gatzweiler、Peter Weuster

  DOI：10.1055/s-1990-27080

  日期：——

  The synthesis of simple alkyl substituted spiroacetals by α,α′-alkylation of metalated acetone dimethylhydrazone with appropriate electrophiles and subsequent acid catalyzed cleavage and ring closure of the products is described.

  通过合适的亲电试剂与金属化丙酮二甲基脲的α,α′-烷基化反应，随后进行酸催化的断裂和环化闭合，描述了简单烷基取代螺缩醛的合成方法。
• Studies on reductive alkylation: Synthesis of Wieland-Miescher ketone analogues bearing an oxygenated angular substituent
  作者：L.N. Mander、R.J. Hamilton

  DOI：10.1016/s0040-4039(01)82080-3

  日期：1981.1

  Wieland-Miescher analogues 2a and 2b have been prepared in good yield by a sequence utilising reductive alkylation of the dihydro aromatic ester enolate 7d, which functions as a synthetic equivalent of the dioxo ester 5 anion; these analogues are envisaged as intermediates in a projected synthesis of bruceantin.

  Wieland-Miescher类似物2a和2b已经通过利用二氢芳族酯烯酸酯7d的还原烷基化的序列以高收率制备，所述二氢芳族酯烯酸酯7d用作二氧代酯5阴离子的合成当量。这些类似物被设想为布鲁青素的预期合成中的中间体。
• Spiroacetals and Other Venom Constituents as Potential Wasp Attractants
  作者：Roderick J. Weston、Anthony D. Woolhouse、Eric B. Spurr、Richard J. Harris、D. Max Suckling

  DOI：10.1023/b:joec.0000006396.55680.b6

  日期：1997.3

  The major volatile spiroacetals from the venom of both the common wasp, Vespula vulgaris and the German wasp V. germanica, viz. 7-methyl-1,6-dioxaspiro[4,5]decane and 7-ethyl-2-methyl-1,6-dioxaspiro[4,5]decane, respectively, were synthesized by known methods. These acetals, along with N-isopentylacetamide (the major volatile amide from wasp venom), 2-heptanone (a honeybee pheromone), 2-methyl-3-buten-2-ol (a component of hornet venom), cuticle wax from V. vulgaris, and venom sacs from both wasp species were assayed by EAG and olfactory bioassay for attractancy to V. vulgaris workers. Antennal responses to all test chemicals were recorded. Acetal isomers (+/-)-2 and (+/-)-3, N-isopentylacetamide, and 2-heptanone were attractive to V. vulgaris workers at levels of <1 mu mol. Greater quantities of the same compounds were repellent to V. vulgaris workers.
• Improved methods for the reductive alkylation of methoxybenzoic acids and esters: applications to the synthesis of bicyclic ketones
  作者：Robert J. Hamilton、Lewis N. Mander、S.Paul Sethi

  DOI：10.1016/s0040-4020(01)90577-0

  日期：1986.1

  employed to introduce the elements of a butanone or pentanone side-chain as a prelude to adding a fused six-membered ring, thereby completing the preparation of several analogues of the Wieland-Miescher ketone 4a in which the angular substituent was oxygenated.

  通过金属氨溶液还原一系列甲氧基苯甲酸和酯，然后将得到的1,4-二氢产物原位烷基化或分离并随后烷基化。三种不同类型的烷基碘被用来引入丁酮或戊酮侧链的元素，作为添加稠合六元环的前奏，从而完成了Wieland-Miescher酮4a的几种类似物的制备，其中角取代基被充氧了。