1-[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-cyclohexanol | 58568-20-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-cyclohexanol
• 英文别名: 1-[3-(2-Methyl-1,3-dioxolan-2-yl)propyl]cyclohexan-1-ol
• CAS: 58568-20-0
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: AGQNHJKLPXLJRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  16
• 可旋转键数：
  4
• 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：

  1-[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-cyclohexanol 在 盐酸 、 zinc(II) chloride 作用下， 生成 1-(Pentanon-4'-yl)-1-chlorcyclohexan
  参考文献：
  名称：

  Kuznetsov,N.V.; Myrsina,R.A., Soviet progress in chemistry, 1975, vol. 41, # 12, p. 60 - 63

  摘要：

  DOI：
• 作为产物：
  描述：

  5-氯-2-戊酮 、 环己酮 在 polymer (P-152) supported naphthalene 、 水 、 lithium 作用下， 生成 1-[3-(2-methyl-[1,3]dioxolan-2-yl)-propyl]-cyclohexanol
  参考文献：
  名称：

  聚合物负载的萘催化锂化反应

  摘要：

  在存在下，功能化的单氯化或二氯化材料1a-6a与过量的锂和催化量的萘负载的聚合物（P-152，可通过2-乙烯基萘，苯乙烯和二乙烯基苯的自由基共聚反应轻松制备）进行反应（巴尔比埃型条件）或不不同的亲电子的[我3的SiCl，卜ñ CHO，卜我CHO，苯甲醛，等2 CO，ç（C 3 H ^ 5）2 CO，镨我2 CO，（CH 2）4一氧化碳（CH 2）5水解后，CO，PhCOMe，PhCH = NPh]产生预期的产物1c-6c。催化剂被定量回收并且可以重复使用几次而不会损失其活性。

  DOI：

  10.1016/s0040-4039(97)10774-2

文献信息

• Polymer supported arene-catalysed lithiation reactions
  作者：Cecilia Gómez、Sonia Ruiz、Miguel Yus

  DOI：10.1016/s0040-4020(99)00330-0

  日期：1999.5

  The reaction of functionalised mono or dichlorinated materials 1a–6a with an excess of lithium and a catalytic amount of a naphthalene (PN) or biphenyl (PB) supported polymer (eassily prepared by radical copolymerisation of 2-vinylnaphthalene or 4-vinylbiphenyl with vinylbenzene and divinylbenzene) in THF either in the presence or not of different electrophiles [Me3SiCl, iPrCHO, PhCHO, Et2CO, (CH2)4CO

  官能化的单或二氯化材料的反应1A-6A与过量锂和萘的催化量（P Ñ）或联苯（P乙支持）聚合物（由2-乙烯基萘或4-乙烯基联苯与自由基共聚eassily制备THF中存在或不存在不同的亲电试剂[Me 3 SiCl，i PrCHO，PhCHO，Et 2 CO，（CH 2）4 CO，（CH 2）5 CO，（c -C 3 H 5））2 CO，i Pr 2用水水解后，在−78或−50°C的温度下，CO，PhCOMe，PhCHnNPh]会产生预期的功能化产物1ca-6ck。聚合物催化剂被定量回收并且可以重复使用几次而没有任何活性损失。
• Polymer supported naphthalene-catalysed lithiation reactions
  作者：Cecilia Gómez、Sonia Ruiz、Miguel Yus

  DOI：10.1016/s0040-4039(97)10774-2

  日期：1998.3

  The reaction of functionalised mono or dichlorinated materials 1a–6a with an excess of lithium and a catalytic amount of a naphthalene supported polymer (P-152, easily prepared by radical copolymerisation of 2-vinylnaphthalene, styrene and divinylbenzene) in THF either in the presence (Barbier-type conditions) or not of different electrophiles [Me3SiCl, BunCHO, BuiCHO, PhCHO, Et2CO, c(C3H5)2CO, Pri2CO

  在存在下，功能化的单氯化或二氯化材料1a-6a与过量的锂和催化量的萘负载的聚合物（P-152，可通过2-乙烯基萘，苯乙烯和二乙烯基苯的自由基共聚反应轻松制备）进行反应（巴尔比埃型条件）或不不同的亲电子的[我3的SiCl，卜ñ CHO，卜我CHO，苯甲醛，等2 CO，ç（C 3 H ^ 5）2 CO，镨我2 CO，（CH 2）4一氧化碳（CH 2）5水解后，CO，PhCOMe，PhCH = NPh]产生预期的产物1c-6c。催化剂被定量回收并且可以重复使用几次而不会损失其活性。
• 2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane: New masked lithium bishomoenolates in the synthesis of bifunctionalized compounds
  作者：Diego J. Ramón、Miguel Yus

  DOI：10.1016/s0040-4039(00)97465-3

  日期：——

  2-(3-Lithiopropyl)- and 2-(3-lithiopropyl)-2-methyl-1,3-dioxolane (2) are prepaned by lithiation of the corresponding chlorinated precursors with lithium naphthalenide at −78°C. The reaction of these masked bishomoenolates with different electrophiles yields the expected monoprotected functional carbonyl compounds (3–12), which can be easily deprotected under acid conditions.

  通过在-78℃下用萘二甲酸锂对相应的氯化前体进行锂化来预沉积2-（3-Lithiopropyl）-和2-（3-lithiopropyl）-2-甲基-1,3-二氧戊环（2）。这些被掩盖的双歧烯酸酯与不同的亲电试剂的反应产生了预期的单保护的羰基官能化合物（3-12），在酸性条件下可以很容易地对其进行脱保护。
• Arene-catalysed lithiation reactions with lithium at low temperature
  作者：Miguel Yus、Diego J. Ramón

  DOI：10.1039/c39910000398

  日期：——

  The reaction of functionalized alkyl chlorides or phenyl sulphides with an excess of lithium powder in the presence of a catalytic amount of an arene (1%; naphthalene, biphenyl, 4,4′-di-tert-butylbiphenyl) in tetrahydrofuran (THF) at –78 °C gives the corresponding organolithium compounds, which react with electrophiles such as water, iso-butyraldehyde, or cyclohexanone to yield the expected reaction products.

  官能化的烷基氯化物或苯基硫化物与过量的锂粉在催化量的炔类（1%；萘、联苯、4,4′-二叔丁基联苯）存在下于-78 °C的四氢呋喃（THF）中反应，得到相应的有机锂化合物，这些化合物与水、异丁醛或环己酮等亲电物反应，得到预期的反应产物。
• Masked lithium bishomoenolates: useful intermediates in organic synthesis
  作者：Diego J. Ramon、Miguel Yus

  DOI：10.1021/jo00012a012

  日期：1991.6

  The lithiation of the chloro ketals 9 with lithium naphthalenide at -78-degrees-C led to the corresponding masked lithium bishomoenolates 4, which are stable species under these conditions and react with different electrophilic reagents (H2O, D2O, i-PrCHO, PhCHO, MeCOEt, (activated CH2)4CO, (activated CH2)5CO, (activated CH2)7CO, PhCOMe, c-C3H5COPh, PhCN, HCONMe2, PrCO activated N(CH2)4, PhCO activated N(CH2)4, PhCOCl, EtOCOCl, PhCHNPh, and (PhCH2S)2) to give, after hydrolysis with water, the corresponding bifunctionalized compounds 10a-22a, 10b-22b, and 10c-15c. When alkyl halides were used as electrophiles the reaction failed. In the presence of a catalytic amount of the complex CuBr.Me2S, the same reaction with alpha,beta-unsaturated ketones (methyl vinyl ketone or 2-cyclohexanone) yielded the expected products of a 1,4-addition 25a-c and 26b. The deprotection of the masked carbonyl group was easily done by treatment with 2 N hydrochloric acid in THF, so as examples, compounds 27a-29a, 30b, 31b, 32c, and 33c were isolated. The transformation of hemiacetals of the type 27a into substituted tetrahydropyrans was carried out by means of compounds of the type R3SiNu (Nu = H, allyl, CN) in the presence of BF3, so products 34a-41a, 42b, and 43b were prepared. Finally, the in situ oxidation of the deprotected products of the type 27a-arising from the reaction of bishomoenolate 4a with carbonyl compounds-with Jones reagent (for ketones derivatives) or PCC (for aldehydes derivatives) led to the corresponding delta-lactones 44-57.