4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol | 14739-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol
• 英文别名: 4-(2,2-dimethyl-1,3-dioxolan-4-yl)butan-1-ol；4-(2,2-dimethyl-1,3-dioxolan-4-yl)butanol
• CAS: 14739-10-7
• 化学式: C₉H₁₈O₃
• 分子量: 174.24
• InChiKey: CRKMKGQWAGRYDY-UHFFFAOYSA-N

物化性质

• 沸点：
  118 °C(Press: 5 Torr)
• 密度：
  0.982±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  12
• 可旋转键数：
  4
• 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：

  4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol 在 氯化亚砜 、 potassium carbonate 、 三乙胺 作用下， 以 甲苯 为溶剂， 生成 4-(4-chlorobutyl)-2,2-dimethyl-1,3-dioxolane
  参考文献：
  名称：

  Medicaments, vicinal dihydroxyalkylxanthines contained therein,

  摘要：

  式为##STR1##的化合物，其中R.sup.1、R.sup.2或R.sup.3中的一个代表具有4至8个碳原子的直链烷基基团，且在.ω.、.ω.-1或.ω.-1、.ω.-2位置具有两个邻位羟基基团，而另外两个基团代表在R.sup.1和R.sup.3位置具有长链或支链烷基基团，碳原子数最多为12，在R.sup.2位置最多为4个碳原子，这两个烷基取代物中碳原子的总数最大为14，通过氧化相应的烯基黄嘌呤和使用引入二羟基烷基基团或其前体的化合物进行烷基化制备。二羟基烷基二烷基黄嘌呤适用于治疗梗阻性呼吸道疾病。

  公开号：

  US04616020A1
• 作为产物：
  描述：

  4-(2',2'-Dimethyl-1',3'-dioxolan-4'-yl)butyl acetate 在 potassium carbonate 作用下， 以 甲醇 、 丙酮 为溶剂， 反应 3.0h， 以96%的产率得到4-(2,2-dimethyl-1,3-dioxolane-4-yl)-1-butanol
  参考文献：
  名称：

  Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations

  摘要：

  A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable gamma-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of;enantioselective features is immediate. The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.

  DOI：

  10.1021/jo00089a034

文献信息

• Regioselective (phenylcarbamoyl)ation of polyhydroxy compounds by phenyl isocyanate-zinc naphthenate
  作者：Shigeyoshi Nishino、Yoshiharu Ishido

  DOI：10.1016/s0008-6215(00)90142-3

  日期：1986.11

  In the presence of zinc naphthenate as the catalyst, the reaction of phenyl isocyanate with 1,2-propanediol and 3,4-O-isopropylidene-d-mannitol gave the primary phenylcarbamates in high yield. 1,2,6-Hexanetriol was selectively phenylcarbamoylated at O-1, and N6-benzyladenosine at O-2′. The common methyl aldohexo- and aldopento-pyranosides gave the 3-mono(phenylcarbamate)s in fair to excellent yields

  在环烷酸锌存在下，苯基异氰酸酯与1,2-丙二醇和3,4-O-异亚丙基-d-甘露糖醇的反应以高收率得到伯苯基氨基甲酸酯。1,2,6-己三醇在O-1处被选择性苯氨基甲酰化，在O-2'处被N6-苄基腺苷选择性地苯甲酰化。常见的甲基乙二醛和醛糖基-吡喃二糖苷以相当高的产率获得了3-单（苯基氨基甲酸酯），在某些情况下还具有相当比例的2-酯。当不使用锌盐时，O-6是六吡喃糖苷中最活泼的氧原子。
• Hafnium Triflate as a Highly Potent Catalyst for Regio- and Chemoselective­ Deprotection of Silyl Ethers
  作者：Shan-Shan Gong、Qi Sun、Xiu-An Zheng、Rui Kong、Hua-Shan Huang、Jing-Ying Wei、Ji-Zong Chen

  DOI：10.1055/s-0037-1610307

  日期：2019.2

  3° alkyl and aryl tert-butyldimethylsilyl (TBS) ethers are significantly different, ranging from 0.05 mol% to 3 mol%, regioselective deprotection of TBS could be easily implemented. Moreover, chemoselective cleavage of different silyl ethers or removal of TBS in the presence of most hydroxyl protecting groups was also accomplished. NMR analyses of silyl products from TBS deprotection indicated that Hf(OTf)4-catalyzed

  摘要 作为IVB族过渡金属路易斯酸，三氟甲磺酸[[Hf（OTf）4 ]在脱甲硅烷基化反应中表现出极高的效能。由于1°，2°，3°烷基和芳基叔丁基二甲基甲硅烷基（TBS）醚的脱保护所需的Hf（OTf）4的量显着不同，范围为0.05 mol％至3 mol％，因此TBS的区域选择性脱保护可以轻松实现。此外，还实现了在大多数羟基保护基存在下，不同甲硅烷基醚的化学选择性裂解或TBS的去除。来自TBS脱保护的甲硅烷基产物的NMR分析表明，取决于所使用的溶剂，Hf（OTf）4催化的甲硅烷基化可能通过不同的机理进行。 作为IVB族过渡金属路易斯酸，三氟甲磺酸[[Hf（OTf）4 ]在脱甲硅烷基化反应中表现出极高的效能。由于1°，2°，3°烷基和芳基叔丁基二甲基甲硅烷基（TBS）醚的脱保护所需的Hf（OTf）4的量显着不同，范围为0.05 mol％至3 mol％，因此TBS的区域选择性脱保护可以轻松实现。此
• One-pot, two-step synthesis of unnatural α-amino acids involving the exhaustive aerobic oxidation of 1,2-diols
  作者：Haruki Inada、Keisuke Furukawa、Masatoshi Shibuya、Yoshihiko Yamamoto

  DOI：10.1039/c9cc07889d

  日期：——

  Herein, we report the nor-AZADO-catalyzed exhaustive aerobic oxidations of 1,2-diols to α-keto acids. Combining oxidation with transamination using dl-2-phenylglycine led to the synthesis of free α-amino acids (AAs) in one pot. This method enables the rapid and flexible preparation of a variety of valuable unnatural AAs, such as fluorescent AAs, photoactivatable AAs, and other functional AAs for bioorthogonal

  在本文中，我们报道了1，2-二醇在α-酮酸的催化作用下也没有进行AZADO催化的详尽的有氧氧化。使用dl-2-苯基甘氨酸将氧化与氨基转移结合在一起，可在一锅中合成游离的α-氨基酸（AAs）。这种方法能够快速灵活地制备各种有价值的非天然AA，例如荧光AA，可光活化的AA和其他用于生物正交反应的功能性AA。
• Facile Cleavage of Silyl Protecting Groups with Catalytic Amounts of FeCl₃
  作者：Yikang Wu、Yong-Qing Yang、Jia-Rong Cui、Lin-Gui Zhu、Ya-Ping Sun

  DOI：10.1055/s-2006-926256

  日期：——

  A very mild and environmentally benign method for ­removal of silyl protecting groups using catalytic amounts of iron ion in MeOH is presented. The method is particularly effective for cleaving triethylsilyl (TES) protecting groups.

  本文介绍了一种温和且环境友好的方法，使用催化量的铁离子在甲醇中去除硅烷保护基团。该方法特别有效地裂解了三乙基硅烷（TES）保护基团。
• Chemoselective Conversion from α-Hydroxy Acids to α-Keto Acids Enabled by Nitroxyl-Radical-Catalyzed Aerobic Oxidation
  作者：Keisuke Furukawa、Haruki Inada、Masatoshi Shibuya、Yoshihiko Yamamoto

  DOI：10.1021/acs.orglett.6b01964

  日期：2016.9.2

  The chemoselective oxidation of α-hydroxy acids to α-keto acids catalyzed by 2-azaadamantane N-oxyl (AZADO), a nitroxyl radical catalyst, is described. Although α-keto acids are labile and can easily release CO2 under oxidation conditions, the use of molecular oxygen as a cooxidant enables the desired chemoselective oxidation.

  描述了由2-氮杂金刚烷N-氧基（AZADO）（一种硝基氧基自由基催化剂）催化的α-羟基酸到α-酮酸的化学选择性氧化。尽管α-酮酸不稳定并且可以在氧化条件下轻易释放CO 2，但是使用分子氧作为助氧化剂可以实现所需的化学选择性氧化。