1-Ethoxy-2,2-difluoro-1-propanol | 165544-23-0

• 分子结构分类: 有机化合物 - 有机卤素化合物 - 卤代醇
• 英文名称: 1-Ethoxy-2,2-difluoro-1-propanol
• 英文别名: 1-ethoxy-2,2-difluoropropan-1-ol
• CAS: 165544-23-0
• 化学式: C₅H₁₀F₂O₂
• 分子量: 140.13
• InChiKey: OOIBOKXAJFUVOD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  9
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  29.5
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  硝基甲烷 、 1-Ethoxy-2,2-difluoro-1-propanol 在 sodium carbonate 作用下， 生成 3,3-Difluoro-1-nitrobutan-2-ol
  参考文献：
  名称：

  The Influence of Fluoroalkyl-Group Electronegativity on Stereocontrol in the Synthesis of Ψ[CH(R_F)NH]Gly Peptides

  摘要：

  新型肽类仿生物分子已合成，这些分子具有不同氟化程度的CH(RF)NH单元，作为肽键的替代物。合成的关键步骤是选择性地将手性α-氨基酸酯与β-氟烷基-α-硝基乙烯进行氮的迈克尔加成。该过程的反式选择性受到氟化基团RF在β位的电负性影响，而非空间位阻的影响。当将RF的单个氟原子替换为氢或甲基时，立体控制能力急剧下降，而Br、Cl和CF3虽然比F体积更大，但在立体控制方面的结果更差。

  DOI：

  10.1055/s-2008-1072653
• 作为产物：
  描述：

  丙酮酸乙酯 、 alkaline earth salt of/the/ methylsulfuric acid 在 sodium tetrahydroborate 、 (diethylamido)sulfur trifluoride 作用下， 以 甲醇 为溶剂， 反应 1.5h， 生成 1-Ethoxy-2,2-difluoro-1-propanol
  参考文献：
  名称：

  Conversion of .alpha.-Keto Esters into .beta.,.beta.-Difluoro-.alpha.-keto Esters and Corresponding Acids: A Simple Route to a Novel Class of Serine Protease Inhibitors

  摘要：

  The preparation of a series of beta,beta-difluoro-alpha-keto esters and corresponding acids RCF(2)COCO(2)R' (R = Me, Et; i-Pr, Bn, and Ph; R' = Et and H), designed as potential inhibitors of serine proteases, is described. The standard procedure developed consists in the initial formation of an alpha,alpha-difluoro ester from an alpha-keto ester, followed by a simple four-step sequence involving the synthesis of hemiacetal, cyanohydrin, and alpha-hydroxy ester difluorinated intermediates. This method provides an easy route to beta,beta-difluoro-alpha-keto esters and corresponding acids, via ''formal'' insertion of a difluoromethylene group between the R substituent and the alpha-carbonyl group of a generic alpha-keto ester.

  DOI：

  10.1021/jo00121a040

文献信息

• [EN] SELECTIVE KINASE INHIBITORS<br/>[FR] INHIBITEURS SÉLECTIFS DE KINASES
  申请人：PORTOLA PHARM INC

  公开号：WO2013078468A1

  公开（公告）日：2013-05-30

  Provided are pyrimidine compounds for inhibiting of Syk kinase, intermediates used in making such compounds, methods for their preparation, pharmaceutical compositions thereof, methods for inhibition Syk kinase activity, and methods for treating conditions mediated at least in part by Syk kinase activity.

  提供了用于抑制Syk激酶的嘧啶化合物，用于制备这些化合物的中间体，其制备方法，药物组合物，抑制Syk激酶活性的方法，以及治疗至少部分由Syk激酶活性介导的疾病的方法。
• TAXANE COMPOUND WITH AZETIDINE RING STRUCTURE
  申请人：Daiichi Sankyo Company, Limited

  公开号：EP1942109A1

  公开（公告）日：2008-07-09

  A compound represented by the general formula (1) [X1 and X2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, R1 represents a phenyl group, R2 represents an alkyl group, an alkenyl group, or an alkoxy group, R3 represents hydrogen atom, a halogen atom, hydroxyl group, or an alkoxy group, R4 represents hydrogen atom, or an alkyl group, Z1 and Z2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, Z3 represents cyano group, an alkyl group, an alkenyl group and the like, Z4 represents an alkyl group, an alkenyl group, an alkynyl group and the like, and ---- represents a single bond or a double bond], which shows high antitumor effect against cancer cells including drug resistant cells.

  一个由通式（1）表示的化合物，其中[X1和X2代表氢原子，卤素原子，羟基等，R1代表苯基，R2代表烷基，烯基或烷氧基，R3代表氢原子，卤素原子，羟基或烷氧基，R4代表氢原子或烷基，Z1和Z2代表氢原子，卤素原子，羟基等，Z3代表氰基，烷基，烯基等，Z4代表烷基，烯基，炔基等，----代表单键或双键]，对包括药物耐药细胞在内的癌细胞表现出高抗肿瘤效果。
• Taxane Compound Having Azetidine Ring Structure
  申请人：Uoto Kouichi

  公开号：US20090186868A1

  公开（公告）日：2009-07-23

  A compound represented by the general formula (1) [X 1 and X 2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, R 1 represents a phenyl group, R 2 represents an alkyl group, an alkenyl group, or an alkoxy group, R 3 represents hydrogen atom, a halogen atom, hydroxyl group, or an alkoxy group, R 4 represents hydrogen atom, or an alkyl group, Z 1 and Z 2 represent hydrogen atom, a halogen atom, hydroxyl group and the like, Z 3 represents cyano group, an alkyl group, an alkenyl group and the like, Z 4 represents an alkyl group, an alkenyl group, an alkynyl group and the like, and represents a single bond or a double bond], which shows high antitumor effect against cancer cells including drug resistant cells.

  一种化合物由通式（1）表示 [其中X1和X2代表氢原子、卤素原子、羟基等，R1代表苯基，R2代表烷基、烯基或烷氧基，R3代表氢原子、卤素原子、羟基或烷氧基，R4代表氢原子或烷基，Z1和Z2代表氢原子、卤素原子、羟基等，Z3代表氰基、烷基、烯基等，Z4代表烷基、烯基、炔基等，且表示单键或双键]，对包括耐药细胞在内的癌细胞具有高抗肿瘤效果。
• Conversion of .alpha.-Keto Esters into .beta.,.beta.-Difluoro-.alpha.-keto Esters and Corresponding Acids: A Simple Route to a Novel Class of Serine Protease Inhibitors
  作者：Melchiorre F. Parisi、Giuseppe Gattuso、Anna Notti、Francisco M. Raymo、Robert H. Abeles

  DOI：10.1021/jo00121a040

  日期：1995.8

  The preparation of a series of beta,beta-difluoro-alpha-keto esters and corresponding acids RCF(2)COCO(2)R' (R = Me, Et; i-Pr, Bn, and Ph; R' = Et and H), designed as potential inhibitors of serine proteases, is described. The standard procedure developed consists in the initial formation of an alpha,alpha-difluoro ester from an alpha-keto ester, followed by a simple four-step sequence involving the synthesis of hemiacetal, cyanohydrin, and alpha-hydroxy ester difluorinated intermediates. This method provides an easy route to beta,beta-difluoro-alpha-keto esters and corresponding acids, via ''formal'' insertion of a difluoromethylene group between the R substituent and the alpha-carbonyl group of a generic alpha-keto ester.
• The Influence of Fluoroalkyl-Group Electronegativity on Stereocontrol in the Synthesis of <i>Ψ</i>[CH(R_F)NH]Gly Peptides
  作者：Alessandro Volonterio、Matteo Zanda、Serena Bigotti

  DOI：10.1055/s-2008-1072653

  日期：——

  New peptidomimetics featuring CH(RF)NH units, having different degree of fluorination, as peptide-bond surrogates have been synthesized. The key step in the synthesis consists of a stereoselective aza-Michael addition of chiral α-amino acid esters to β-fluoroalkyl-α-nitroethenes. The diastereoselection of the process was influenced by the electronegativity, rather than by the steric bulk, of the fluorinated residue RF in β-position of the nitroalkene acceptors. Replacement of a single F atom of RF by a hydrogen or methyl group brings about a dramatic drop of stereocontrol, whereas Br, Cl, and CF3, albeit bulkier than F, provide poorer results in terms of stereocontrol.

  新型肽类仿生物分子已合成，这些分子具有不同氟化程度的CH(RF)NH单元，作为肽键的替代物。合成的关键步骤是选择性地将手性α-氨基酸酯与β-氟烷基-α-硝基乙烯进行氮的迈克尔加成。该过程的反式选择性受到氟化基团RF在β位的电负性影响，而非空间位阻的影响。当将RF的单个氟原子替换为氢或甲基时，立体控制能力急剧下降，而Br、Cl和CF3虽然比F体积更大，但在立体控制方面的结果更差。